US5541337A - Substituted 5-alkoxy-1,2,4-triazol-3-(thi)ones - Google Patents

Substituted 5-alkoxy-1,2,4-triazol-3-(thi)ones Download PDF

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US5541337A
US5541337A US08/269,875 US26987594A US5541337A US 5541337 A US5541337 A US 5541337A US 26987594 A US26987594 A US 26987594A US 5541337 A US5541337 A US 5541337A
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sub
alkyl
alkoxy
fluorine
chlorine
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Klaus-Helmut M uller
Klaus K onig
Joachim Kluth
Klaus L urssen
Hans-Joachim Santel
Robert R. Schmidt
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Bayer AG
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Bayer AG
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Priority claimed from US07/556,052 external-priority patent/US5057144A/en
Priority claimed from DE4030063A external-priority patent/DE4030063A1/en
Priority claimed from DE4110795A external-priority patent/DE4110795A1/en
Priority claimed from US07/692,439 external-priority patent/US5094683A/en
Priority claimed from US07/816,365 external-priority patent/US5241074A/en
Priority claimed from US07/976,185 external-priority patent/US5356865A/en
Priority to US08/269,875 priority Critical patent/US5541337A/en
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Assigned to BAYER AKTIENGESELLSCHAFT reassignment BAYER AKTIENGESELLSCHAFT ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: KONIG, KLAUS, SANTEL, HANS-JOACHIM, SCHMIDT, ROBERT R., KLUTH, JOACHIM, LURSSEN, KLAUS, MULLER, KLAUS-HELMUT
Priority to US08/637,995 priority patent/US5652372A/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/12—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/14—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Definitions

  • the invention relates to new substituted 5-alkoxy-1,2,4-triazol-3-(thi)ones, a plurality of several processes, and also new intermediates for their preparation, and their use as herbicides.
  • This invention also relates to intermediates used to prepare new sulphonylaminocarbonyltriazolinones having substituents bonded via oxygen which possess herbicidal activity.
  • the final products are disclosed in application Ser. No. 08/048,026, filed Apr. 15, 1993 incorporated herein by reference.
  • R 2 represents alkyl, alkenyl, alkinyl, halogenoalkyl, halogenoalkenyl, halogenoalkinyl, alkoxyalkyl, cyanoalkyl, alkoxy, cycloalkyl or cycloalkylalkyl,
  • R 3 represents alkyl, alkenyl, alkinyl, halogenoalkyl, halogenoalkenyl, halogenoalkinyl, alkoxyalkyl or cyanoalkyl,
  • X represents oxygen or sulphur
  • R 1 and X have the abovementioned meanings, if appropriate in the presence of a diluent and if appropriate in the presence of a basic reaction auxiliary, or when
  • R 4 represents alkyl, aralkyl or aryl, if appropriate in the presence of a diluent and if appropriate in the presence of a basic reaction auxiliary, or when
  • R 4 represents alkyl, aralkyl or aryl, are reacted with amino compounds of the general formula (VI)
  • R 1 has the abovementioned meaning, if appropriate in the presence of a diluent and if appropriate in the presence of a basic reaction auxiliary.
  • the new compounds of the formula (I) show a considerably better herbicidal activity than the compound 4-amino-5-methyl-2-phenylaminocarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-one, which is known.
  • R 3 represents an optionally substituted radical from the series comprising alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, aralkyl, aryl, and
  • R a represents an optionally substituted radical from the series comprising alkyl, aralkyl, aryl, heteroaryl,
  • Formula (I) provides a general definition of the substituted 5-alkoxy-1,2,4-triazol-3-(thi)ones according to the invention.
  • Preferred compounds of the formula (I) are those in which
  • R 1 represents in each case straight-chain or branched alkyl having 1 to 18 carbon atoms, alkenyl having 2 to 8 carbon atoms, alkinyl having 2 to 8 carbon atoms, halogenoalkyl having 1 to 8 carbon atoms and 1 to 17 identical or different halogen atoms, halogenoalkenyl or halogenoalkinyl, each of which has 2 to 8 carbon atoms and 1 to 15 or 13 identical or different halogen atoms, cyanoalkyl having 1 to 8 carbon atoms, hydroxyalkyl having 1 to 8 carbon atoms and 1 to 6 hydroxyl groups, alkoxyalkyl, alkoximinoalkyl, alkoxycarbonylalkyl or alkoxycarbonylalkenyl, each of which has up to 6 carbon atoms in the individual alkyl or alkenyl moieties, alkylaminoalkyl or dialkylaminoalkyl, each of which has 1 to 6 carbon atoms
  • R 2 represents in each case straight-chain or branched alkyl having 1 to 8 carbon atoms, alkenyl having 2 to 8 carbon atoms, alkinyl having 2 to 8 carbon atoms, halogenoalkyl having 1 to 8 carbon atoms and 1 to 17 identical or different halogen atoms, halogenoalkenyl having 2 to 8 carbon atoms and 1 to 15 identical or different halogen atoms, halogenoalkinyl having 2 to 8 carbon atoms and 1 to 13 identical or different halogen atoms, alkoxyalkyl or alkoxy, each of which has 1 to 6 carbon atoms in the individual alkyl moieties, cyanoalkyl having 1 to 8 carbon atoms, or represents cycloalkylalkyl or cycloalkyl, each of which has 3 to 7 carbon atoms in the cycloalkyl moiety and if appropriate 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety,
  • R 3 represents in each case straight-chain or branched alkyl having 1 to 8 carbon atoms, alkenyl having 2 to 8 carbon atoms, alkinyl having 2 to 8 carbon atoms, halogenoalkyl having 1 to 8 carbon atoms and 1 to 17 identical or different halogen atoms, halogenoalkenyl having 2 to 8 carbon atoms and 1 to 15 identical or different halogen atoms, halogenoalkinyl having 2 to 8 carbon atoms and 1 to 13 identical or different halogen atoms, alkoxyalkyl having 1 to 6 carbon atoms in each of the individual alkyl moieties, or represents cyanoalkyl having 1 to 8 carbon atoms,
  • X represents oxygen or sulphur
  • Y represents oxygen or sulphur and halogen in the substitution patterns mentioned in the case of R 1 , R 2 and R 3 represents fluorine, chlorine, bromine and iodine.
  • Particularly preferred compounds of the formula (I) are those in which
  • R 1 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, in each case straight-chain or branched pentyl, hexyl, heptyl, octyl, nonyl, decyl or dodecyl, or represents allyl, propenyl, n- or i-butenyl, n- or i-pentenyl, n- or i-hexenyl, propargyl, n- or i-butinyl, n- or i-pentinyl, n- or i-hexinyl, or represents straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in particular fluorine, chlorine or bromine, or represents in each case straight-chain or branched halogenoalkenyl or hal
  • R 1 furthermore represents in each case straight-chain or branched alkoxy having 1 to 6 carbon atoms, alkenyloxy having 3 to 6 carbon atoms or alkinyloxy having 3 to 6 carbon atoms, or represents benzyl, phenylethyl, phenylpropyl, phenylbutyl, phenylpentyl, phenylhexyl, phenylheptyl, phenylcyanomethyl, phenylcyanoethyl, phenylcyanopropyl, phenoxymethyl, phenoxyethyl, phenoxypropyl, phenoxymethyl, phenoxyethyl, phenoxypropyl, phenoxymethyl
  • R 2 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n- or i-pentyl, n- or i-hexyl, or represents allyl, propargyl, methoxy, ethoxy, methoxymethyl, ethoxymethyl, methoxyethyl or ethoxyethyl, or represents straight-chain or branched halogenoalkyl, halogenoalkenyl and halogenoalkinyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in particular fluorine, chlorine or bromine, or represents cyclopentyl, cyclohexyl, cyclopropyl, cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl or cyclohexylethyl,
  • R 3 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, n- or i-hexyl, or represents allyl, propargyl, methoxyethyl, ethoxyethyl, fluoroethyl, chloroethyl, fluoropropyl, chloropropyl or cyanoethyl,
  • X represents oxygen or sulphur
  • Y represents oxygen or sulphur.
  • R 1 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, n-, i-, s- or t-hexyl, propargyl, n- or i-butinyl, n- or i-pentinyl, or represents straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 4 identical or different halogen atoms, in particular fluorine and chlorine, or represents cyanomethyl, cyanoethyl or n- or i-cyanopropyl, or represents cyclopropyl, cyclopropylmethyl, cyclopentyl, cyclopentylmethyl, cyclohexyl or cyclohexylmethyl, each of which is optionally monosubstituted to trisubstituted
  • R 2 represents methyl, ethyl, n-, i- or cyclopropyl, n-, i-, s- or t-butyl,
  • R 3 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n- or i-pentyl,
  • Y represents oxygen
  • R a has the abovementioned meaning, if appropriate in the presence of a diluent, or when
  • Z 1 represents halogen, alkoxy, aralkoxy or aryloxy, are reacted with sulphonamides of the general formula (XIII)
  • R a has the abovementioned meaning, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent, or when
  • R a has the abovementioned meaning
  • Z 1 represents halogen, alkoxy, aralkoxy or aryloxy, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent and, if appropriate, salts are formed, by customary methods, of the compounds of the formula (I) which have been prepared by process (a), (b) or (c).
  • the new sulphonylaminocarbonyltriazolinones having substituents bonded via oxygen, of the general formula (I), and their salts are distinguished by a powerful herbicidal activity.
  • the new compounds of the formula (X) show a considerably better herbicidal action than the known compound 2-(2-chlorophenylsulphonylaminocarbonyl)-4,5-dimethyl-2,4-dihydro-3H-1,2,4-triazol-3-one, which has a similar structure.
  • the invention preferably relates to compounds of the formula (X) in which
  • R 2 represents hydrogen, amino, or represents C 1 -C 6 -alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylcarbonyl or C 1 -C 4 -alkoxy-carbonyl, or represents C 3 -C 6 -alkenyl or C 3 C 6 -alkinyl, each of which is optionally substituted by fluorine, chlorine and/or bromine, or represents C 3 -C 6 -cycloalkyl which is optionally substituted by fluorine, chlorine, bromine and/or C 1 -C 4 -alkyl, or represents phenyl-C 1 -C 3 -alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C 1 -C 4 -alkyl, trifluoromethyl, C 1 -C 4 -alkoxy and/or C 1 -C 4
  • R 3 represents C 1 -C 6 -alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -alkoxycarbonyl, or represents C 3 -C 6 -alkenyl or C 3 -C 6 -alkinyl, each of which is optionally substituted by fluorine, chlorine and/or bromine, or represents C 3 -C 6 -cycloalkyl which is optionally substituted by fluorine, chlorine, bromine and/or C 1 -C 4 -alkyl, or represents cyclohexenyl, or represents phenyl-C 1 -C 3 -alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C 1 -C 4 -alkyl, trifluoromethyl, C 1 -C 4 -alkoxy and/or C 1
  • R a represents the group ##STR13## in which R 4 .spsp.1 and R 5 are identical or different and represent hydrogen, fluorine, chlorine, bromine, iodine, nitro, C 1 -C 6 -alkyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkylamino-carbonyl, di- (C 1 -C 4 -alkyl) amino-carbonyl, hydroxyl, C 1 -C 4 -alkoxy, formyloxy, C 1 -C 4 -alkyl-carbonyloxy, C 1 -C 4 -alkoxy-carbonyloxy, C 1 -C 4 -alkylamino-carbonyloxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4
  • p represents the numbers 1 or 2 and
  • R 6 represents C 1 -C 4 -alkyl (which is optionally substituted by fluorine, chlorine, bromine, cyano or C 1 -C 4 -alkoxy-carbonyl), C 3 -C 6 -alkenyl, C 3 -C 6 -alkinyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkylamino, C 1 -C 4 -alkylamino, di-(C 1 -C 4 -alkyl)-amino, phenyl or the radical --NHOR 7 where
  • R 7 represents C 1 -C 12 -alkyl (which is optionally substituted by fluorine, chlorine, cyano, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -alkyl-carbonyl, C 1 -C 4 -alkoxy-carbonyl, C 1 -C 4 -alkylamino-carbonyl or di-(C 1 -C 4 -alkyl)-amino-carbonyl), or represents C 3 -C 6 -alkenyl (which is optionally substituted by fluorine, chlorine or bromine),C 3 -C 6 -alkinyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 2 -alkyl, phenyl
  • R 4 .spsp.1 and/or R 5 furthermore represent phenyl or phenoxy, or represent C 1 -C 4 -alkylcarbonylamino, C 1 -C 4 -alkoxy-carbonylamino, C 1 -C 4 -alkylamino-carbonyl-amino, di-(C 1 -C 4 -alkyl)-amino-carbonylamino, or the radical --CO--R 8 where
  • R 8 represents C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 3 -C 6 -cycloalkoxy, C 3 -C 6 -alkenyloxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylamino, C 1 -C 4 -alkoxyamino, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl-amino or di-(C 1 -C 4 -alkyl)-amino (which are optionally substituted by fluorine and/or chlorine),
  • R 4 .spsp.1 and/or R 5 furthermore represent trimethylsilyl, thiazolinyl, C 1 -C 4 -alkylsulphonyloxy, di-(C 1 -C 4 -alkyl)aminosulphonylamino or the radical --CH ⁇ N--R 9 where
  • R 9 represents C 1 -C 6 -alkyl which is optionally substituted by fluorine, chlorine, cyano, carboxyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl or C 1 -C 4 -alkylsulphonyl, or represents benzyl which is optionally substituted by fluorine or chlorine, or represents C 3 -C 6 -alkenyl or C 3 -C 6 -alkinyl, each of which is optionally substituted by fluorine or chlorine, or represents phenyl which is optionally substituted by fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, trifluoromethyl, trifluoromethoxy or trifluoromethylthio, or represents optionally fluorine- and/or chlorine-substituted C 1 -C 6 -alkoxy,
  • R a represents the radical ##STR14## where R 10 represents hydrogen or C 1 -C 4 -alkyl
  • R 11 and R 12 are identical or different and represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, C 1 -C 4 -alkyl (which is optionally substituted by fluorine and/or chlorine), C 1 -C 4 -alkoxy (which is optionally substituted by fluorine and/or chlorine), carboxyl, C 1 -C 4 -alkoxy-carbonyl, dimethylaminocarbonyl, C 1 -C 4 -alkylsulphonyl or di-(C 1 -C 4 -alkyl) -aminosulphonyl;
  • R a represents the radical ##STR15## where R 13 and R 14 are identical or different and represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, C 1 -C 4 -alkyl (which is optionally substituted by fluorine and/or chlorine) or C 1 -C 4 -alkoxy (which is optionally substituted by fluorine and/or chlorine);
  • R a represents the radical ##STR16## where R 15 and R 16 are identical or different and represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, C 1 -C 4 -alkyl (which is optionally substituted by fluorine and/or chlorine), C 1 -C 4 -alkoxy (which is optionally substituted by fluorine and/or chlorine), or represent C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl or C 1 -C 4 -alkylsulphonyl (which are optionally substituted by fluorine and/or chlorine), or represent aminosulphonyl, mono-(C 1 -C 4 -alkyl)-aminosulphonyl, di-(C 1 -C 4 -alkyl)-aminosulphonyl or C 1 -C 4 -alkoxycarbonyl or dimethylaminocarbonyl;
  • R a represents the radical ##STR17## where R 17 and R 18 are identical or different and represent hydrogen, fluorine, chlorine, bromine, C 1 -C 4 -alkyl (which is optionally substituted by fluorine and/or bromine), C 1 -C 4 -alkoxy (which is optionally substituted by fluorine and/or chlorine), C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl or C 1 -C 4 -alkylsulphonyl (which are optionally substituted by fluorine and/or chlorine), or represent di-(C 1 -C 4 -alkyl)-aminosulphonyl;
  • R a represents the radical ##STR18## where R 19 and R 20 are identical or different and represent hydrogen, fluorine, chlorine, bromine, cyano, nitro, C 1 -C 4 -alkyl (which is optionally substituted by fluorine and/or chlorine), C 1 -C 4 -alkoxy (which is optionally substituted by fluorine and/or chlorine), C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl or C 1 -C 4 -alkylsulphonyl (which is optionally substituted by fluorine and/or chlorine), di-(C 1 -C 4 -alkyl)-amino-sulphonyl, C 1 -C 4 -alkoxy-carbonyl or dimethylaminocarbonyl, and
  • A represents oxygen, sulphur or the group N--Z 1 , where
  • Z 1 represents hydrogen, C 1 -C 4 -alkyl (which is optionally substituted by fluorine, chlorine, bromine or cyano), C 3 -C 6 -cycloalkyl, benzyl, phenyl (which is optionally substituted by fluorine, chlorine, bromine or nitro), C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxy-carbonyl or di-(C 1 -C 4 -alkyl) -aminocarbonyl;
  • R a represents the radical ##STR19## where R 21 and R 22 are identical or different and represent hydrogen, C 1 -C 4 -alkyl, halogen, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxy or C 1 -C 4 -halogenoalkoxy,
  • Y 1 represents sulphur or the group N--R 23 , where
  • R 23 represents hydrogen or C 1 -C 4 -alkyl
  • R a represents the radical ##STR20## where R 24 represents hydrogen, C 1 -C 4 -alkyl, benzyl, pyridyl, quinolinyl or phenyl,
  • R 25 represents hydrogen, halogen, cyano, nitro, C 1 -C 4 -alkyl (which is optionally substituted by fluorine and/or chlorine), C 1 -C 4 -alkoxy (which is optionally substituted by fluorine and/or chlorine), dioxolanyl or C 1 -C 4 -alkoxy-carbonyl and
  • R 26 represents hydrogen, halogen or C 1 -C 4 -alkyl
  • R a represents one of the groups listed below ##STR21##
  • the invention furthermore preferably relates to the sodium, potassium, magnesium, calcium, ammonium, C 1 -C 4 -alkyl-ammonium, di-(C 1 -C 4 -alkyl)-ammonium, tri-(C 1 -C 4 -alkyl)-ammonium, C 5 - or C 6 -cycloalkyl-ammonium and di-(C 1 -C 2 -alkyl) -benzyl-ammonium salts of compounds of the formula (I) in which R 1 , R 2 and R 3 have the meanings mentioned above as being preferred.
  • the invention relates to compounds of the formula (X) in which
  • R 2 represents hydrogen, amino, C 1 -C 4 -alkyl which is optionally substituted by fluorine, cyano, methoxy or ethoxy, or represents allyl, C 3 -C 6 -cycloalkyl, benzyl, phenyl, C 1 -C 3 -alkylamino, C 3 -C 6 -cycloalkylamino or di-(C 1 -C 3 -alkyl) -amino,
  • R 3 represents C 1 -C 4 -alkyl which is optionally substituted by fluorine and/or chlorine, methoxy or ethoxy, or represents C 3 -C 4 -alkenyl which is optionally substituted by fluorine and/or chlorine, or represents C 3 -C 6 -cycloalkyl, or represents benzyl which is optionally substituted by fluorine, chlorine and/or methyl, and
  • R a represents the group ##STR22## where R 4 .spsp.1 represents fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy, 2-chloro-ethoxy, 2-methoxyethoxy, C 1 -C 3 -alkylthio, C 1 -C 3 -alkylsulphinyl, C 1 -C 3 -alkylsulphonyl, dimethylaminosulphonyl, diethylaminosulphonyl, N-methoxy-N-methylaminosulphonyl, methoxyaminosulphonyl, phenyl, phenoxy or C 1 -C 3 -alkoxy-carbonyl and
  • R 5 represents hydrogen, fluorine, chlorine or bromine
  • R a represents the radical ##STR23## where R 10 represents hydrogen
  • R 11 represents fluorine, chlorine, bromine, methyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylsulphonyl or dimethylaminosulphonyl and
  • R 12 represents hydrogen
  • R a represents the radical ##STR24## where R represents C 1 -C 4 -alkyl, or represents the radical ##STR25## where R represents C 1 -C 4 -alkyl.
  • radicals in general or mentioned in preferred ranges, can be combined with each other in any desired way, that is to say also between the particular preferred ranges.
  • Formula (II) provides a general definition of the 5-alkoxy-1,2,4-triazol-3-(thi)ones to be used as starting substances in processes (a) and (b) according to the invention for the preparation of compounds of the formula (I).
  • R 2 , R 3 and Y preferably, or in particular, have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention as being preferred, or as particularly preferred, for R 2 , R 3 and Y.
  • Formula (II) provides a general definition of the triazolinones to be used as starting substances in processes (a) and (c) according to the invention for the preparation of compounds of the formula (X).
  • R 2 and R 3 preferably, or in particular, have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (X) according to the invention as being preferred, or particularly preferred, for R 2 and R 3 .
  • R 4 has the abovementioned meaning are reacted with alkyliminocarboxylic diesters of the general formula (VIII) ##STR124## in which R 2 and R 3 have the abovementioned meaning, if appropriate in the presence of a diluent such as, for example, o-dichlorobenzene, at temperatures between 0° C. and 200° C., preferably between 50° C. and 150° C. (cf. the Preparation Examples).
  • a diluent such as, for example, o-dichlorobenzene
  • Formula (III) provides the general definition of the iso(thio)cyanates to be used as starting substances in process (a) according to the invention for the preparation of compounds of the formula (I).
  • R 1 and X preferably, or in particular, have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention as being preferred, or as particularly preferred, for R 1 and X.
  • the starting substances of the formula (III) are known chemicals for organic synthesis.
  • Formula (IV) provides a general definition of the reactive (thio)carbamates to be used as starting substances in process (b) according to the invention for the preparation of compounds of the formula (I).
  • R 1 and X preferably, or in particular, have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention as being preferred, or as particularly preferred, for R 1 and X;
  • R 4 preferably represents methyl, ethyl, phenyl or benzyl.
  • the starting substances of the formula (IV) are known chemicals for organic synthesis.
  • R 2 , R 3 , X and Y preferably, or in particular, have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention as being preferred, or as particularly preferred, for R 2 , R 3 , X and Y;
  • R 4 preferably represents methyl, ethyl, phenyl or benzyl.
  • Formula (VI) provides a general definition of the amino compounds furthermore to be used as starting substances in process (c) according to the invention for the preparation of compounds of the formula (I).
  • Processes (a), (b) and (c) according to the invention for the preparation of the new compounds of the formula (I) are preferably carried out in each case using diluents.
  • Suitable diluents for this purpose are virtually all inert organic solvents.
  • aliphatic and aromatic, optionally halogenated hydrocarbons such as pentane, hexane, heptane, cyclohexane, petroleum ether, benzine, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, ethers such as diethyl ether and dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane, ketones such as acetone, methyl ethyl ketone, methyl isopropyl ketone and methyl isobutyl ketone, esters such as methyl acetate and ethyl acetate, nitriles such as, for example, acetonitrile and propionitrile, amides such as
  • processes (a), (b) and (c) according to the invention are in each case carried out in the presence of a basic reaction auxiliary.
  • Suitable substances which are employed are preferably basic organic nitrogen compounds. These include, for example, trimethylamine, triethylamine, tripropylamine, tributylamine, diisopropylamine, dicyclohexylamine, N,N-dimethylaniline, N,N-dimethylbenzylamine, pyridine, 4-dimethylamino-pyridine, 1,5-diazabicyclo-(4,3,0]-non-5-ene (DBN), 1,8-diazabicyclo[5,4,0)-undec-7-ene (DBU) and 1,4-diazabicyclo-[2,2,2]-octane (DABCO).
  • DBN 1,5-diazabicyclo-(4,3,0]-non-5-ene
  • DBU 1,8-diazabicyclo[5,4,0)-
  • reaction temperatures can be varied in each case in a substantial range.
  • the processes are carried out at temperatures between -20° C. and 150° C., preferably at temperatures between 0° C. and 100° C.
  • the starting substances required in each case are generally employed in approximately equimolar amounts. However, it is also possible to use one of the two components employed in each case in a larger excess.
  • the reactions are carried out in a suitable diluent in the presence of a basic reaction auxiliary, and the reaction mixture is stirred for several hours at the particular temperature required.
  • Working-up in the processes according to the invention is carried out in each case by customary methods.
  • R 4 .spsp.1 has the abovementioned meaning are reacted with alkyliminocarbonic diesters of the general formula (XVI) ##STR127## in which R 2 and R 3 have the abovementioned meaning, if appropriate in the presence of a diluent such as, for example, methanol, at temperatures between 0° C. and 50° C., and the compounds formed in this process, of the general formula (XVII) ##STR128## in which R 2 , R 3 and R 4 .spsp.1 have the abovementioned meaning, are, if appropriate, isolated by customary methods and heated to temperatures between 50° C. and 150° C., if appropriate in the presence of a diluent such as, for example, toluene, xylene or o-dichlorobenzene (cf. Preparation Examples).
  • a diluent such as, for example, toluene, xylene or
  • Formula (XI) provides a general definition of the sulphonyl isocyanates furthermore to be used as starting substances in process (a) according to the invention for the preparation of compounds of the formula (X).
  • R a preferably, or in particular, has that meaning which has already been mentioned above in connection with the description of the compounds of the formula (X) according to the invention as being preferred, or particularly preferred, for R a .
  • Examples of the starting substances of the formula (XI) which may be mentioned are: 2-fluoro-, 2-chloro-, 2-bromo-, 2-methyl-, 2-methoxy-, 2-trifluoromethyl-, 2-difluoro-methoxy-, 2-trifluoromethoxy-, 2-methylthio-, 2-ethylthio-, 2-propylthio-, 2-methylsulphinyl-, 2-methylsulphonyl-, 2-dimethylaminosulphonyl-, 2-diethylaminosulphonyl-, 2-(N-methoxy-N-methyl)-aminosulphonyl-, 2-phenyl-, 2-phenoxy-, 2-methoxycarbonyl-, 2-ethoxycarbonyl-, 2-propoxycarbonyl- and 2-isopropoxycarbonyl-phenylsulphonyl isocyanate, 2-fluoro-, 2-chloro-, 2-difluoromethoxy-, 2-trifluoromethoxy-, 2-me
  • Process (a) according to the invention for the preparation of the new compounds of the formula (X) is preferably carried out using diluents.
  • Diluents which are suitable for this purpose are virtually all inert organic solvents. These preferably include aliphatic and aromatic, optionally halogenated hydrocarbons such as pentane, hexane, heptane, cyclohexane, petroleum ether, benzine, ligroine, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, ethers such as diethyl ether and dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane, ketones such as acetone, methyl ethyl ketone, methyl isopropyl ketone and
  • the reactants can be combined in any desired sequence.
  • the reaction mixture is stirred until the reaction is complete and the product is isolated by filtration with suction.
  • the mixture is concentrated, and the crude product which remains in the residue is brought to crystallisation with a suitable solvent such as, for example, diethyl ether.
  • a suitable solvent such as, for example, diethyl ether.
  • the product of the formula (X) which is obtained in this way in crystalline form is isolated by filtration with suction.
  • Formula (XII) provides a general definition of the triazolinone derivatives to be used as starting substances in process (b) according to the invention for the preparation of compounds of the formula (X).
  • R 2 and R 3 preferably, or in particular, have those meanings which have already been mentioned above in connection with description of the compounds of the formula (X) according to the invention as being preferred, or particularly preferred, for R 2 and R 3 and
  • Z 1 preferably represents chlorine, C 1 -C 4 -alkoxy, benzyloxy or phenoxy, in particular methoxy or phenoxy.
  • Examples of the starting substances of the formula (XII) which are possible are the compounds of the formula (XII) which are to be prepared from the compounds of the formula (II) listed in Table 3 and phosgene, methyl chloroformate, benzyl chloroformate, phenyl chloroformate or diphenyl carbonate.
  • Z 2 represents a leaving group such as chlorine, methoxy, benzyloxy or phenoxy
  • a diluent such as, for example, tetrahydrofuran
  • an acid acceptor such as, for example, sodium hydride or potassium tert-butylate
  • Formula (XVIII) provides a general definition of the sulphonamides furthermore to be used as starting substances in process (b) according to the invention for the preparation of compounds of the formula (X).
  • R a preferably, or in particular, has that meaning which has already been mentioned above in connection with the description of the compounds of the formula (X) according to the invention as being preferred, or particularly preferred, for R a .
  • the sulphonamides of the formula (XIII) are known and/or can be prepared by processes known per se (cf. U.S. Pat. Nos. 4,127,405, 4,169,719, 4,371,391; EP-A 7,687, 13,480, 21,641, 23,141, 23,422, 30,139, 35,893, 44,808, 44,809, 48,143, 51,466, 64,322, 70,041, 173,312).
  • Process (b) according to the invention for the preparation of the new compounds of the formula (X) is preferably carried out using diluents.
  • Diluents which are suitable for this purpose are virtually all inert organic solvents as have been indicated, for example, above in the case of process (a) according to the invention.
  • reaction temperatures can be varied within a substantial range.
  • the process is carried out at temperatures between 0° C. and 100° C., preferably at temperatures between 10° C. and 60° C.
  • the starting substances required in each case are generally employed in approximately equimolar amounts. However, it is also possible to use one of the two components employed in each case in a larger excess.
  • the reactions are carried out in a suitable diluent in the presence of an acid acceptor, and the reaction mixture is stirred for several hours at the particular temperature required.
  • Working-up in process (b) according to the invention is carried out in each case by customary methods.
  • Formula (XIV) provides a general definition of the sulphonamide derivatives furthermore to be used as starting substances in process (c) according to the invention for the preparation of compounds of the formula (X).
  • R a and Z 1 preferably, or in particular, have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (X) or (XII) according to the invention as being preferred, or particularly preferred, for R a and Z 1 .
  • Process (c) according to the invention is preferably carried out using diluents.
  • Solvents which are suitable for this purpose are the same organic solvents as have been mentioned above in connection with the description of process (a) according to the invention.
  • process (c) is carried out in the presence of an acid acceptor.
  • Acid-binding agents which are suitable for this purpose are the same as have been mentioned above in connection with the description of process (b) according to the invention.
  • reaction temperatures can vary within a substantial range.
  • the process is carried out at temperatures between 0° C. and 100° C., preferably at temperatures between 10° C. and 60° C.
  • process (c) according to the invention is carried out under atmospheric pressure.
  • the process can also be carried out under increased or reduced pressure.
  • the starting substances required in each case are generally employed in approximately equimolar amounts. However, it is also possible to use one of the two components employed in each case in a larger excess.
  • the reactions are generally carried out in a suitable diluent in the presence of an acid acceptor, and the reaction mixture is stirred for several hours at the particular temperature required.
  • Working-up is carried out in process (c) according to the invention in each case by customary methods.
  • salt formers such as, for example, sodium hydroxide, sodium methylate, sodium ethylate, potassium hydroxide, potassium methylate or potassium ethylate, ammonia, isopropylamine, dibutylamine or triethylamine, in suitable diluents such as, for example, water, methanol or ethanol.
  • suitable diluents such as, for example, water, methanol or ethanol.
  • the active compounds according to the invention can be used as defoliants, desiccants, agents for destroying broad-leaved plants and, especially, as weed-killers.
  • weeds in the broadest sense, there are to be understood all plants which grow in locations where they are undesired. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
  • the active compounds according to the invention can be used, for example, in connection with the following plants:
  • the compounds are suitable, depending on the concentration, for the total combating of weeds, for example on industrial terrain and rail tracks, and on paths and squares with or without tree plantings. Equally, the compounds can be employed for combating weeds in perennial cultures, for example afforestations, decorative tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and hopfields, on lawns, turf and pasture-land, and for the selective combating of weeds in annual cultures.
  • the compounds of the formula (I) according to the invention are suitable for selectively combating monocotyledon and dicotyledon weeds, mainly in monocotyledon cultures, by the pre- and the post-emergence method.
  • Some of the compounds of the formula (X) according to the invention are suitable for total or semi-total weed control, some for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon cultures, both pre-emergence and post-emergence.
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with active compound, and very fine capsules in polymeric substances.
  • formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surface-active agents, that is emulsifying agents and/or dispersing agents and/or foam-forming agents.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • liquid solvents there are suitable in the main: aromatics, such as xylene, toluene, or alkyl-naphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, as well as water.
  • aromatics such as xylene, toluene, or alkyl-naphthalenes
  • solid carriers for example ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as highly disperse silica, alumina and silicates, as solid carriers for granules there are suitable: for example crushed and fractionated natural minerals such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; as emulsifying and/or foam-forming agents there are suitable: for example non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, aryl
  • Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latexes, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations. Further additives can be mineral and vegetable oils.
  • colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs
  • trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • the formulations in general contain between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used as mixtures with known herbicides, finished formulations or tank mixes being possible.
  • Suitable herbicides for the mixtures are known herbicides, such as, for example, 1-amino-6-ethylthio-3-(2,2-dimethylpropyl)-1,3,5-triazine-2,4(1H,3H)-dione (AMETHYDIONE) or N-(2-benzothiazolyl)-N,N'-dimethylurea (METABENZTHIAZURON) for combating weeds in cereals; 4-amino3-methyl-6-phenyl-1,2,4-triazin-5(4H)-one (METAMITRON) for combating weeds in sugar beet and 4-amino-6-(1,1-dimethylethyl)-3-methylthio-1,2,4-triazin-(4H) -one (METRIBUZIN) for combating weeds in soya beans; furthermore also 2,4-dichlorophenoxyacetic acid (2,4-D); 4-(2,4-dichlorophen
  • the active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary manner, for example by watering, spraying, atomising or scattering.
  • the active compounds according to the invention can be applied either before or after emergence of the plants.
  • the amount of active compound used can vary within a substantial range. It depends essentially on the nature of the desired effect. In general, the amounts used are between 1 g and 10 kg of active compound per hectare of soil surface, preferably between 10 g and 5 kg per ha.
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • Test plants which have a height of 5-15 cm are sprayed with the preparation of the active compound in such a way as to apply the particular amounts of active compound desired per unit area.
  • the concentration of the spray liquor is so chosen that the particular amounts of active compound desired are applied in 1000 l of water/ha.
  • the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control.
  • the figures denote: ##EQU1##
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • Seeds of the test plants are sown in normal soil and, after 24 hours, watered with the preparation of the active compound. It is expedient to keep constant the amount of water per unit area.
  • the concentration of the active compound in the preparation is of no importance, only the amount of active compound applied per unit area being decisive.
  • the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control.
  • the figures denote: ##EQU2##
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • Test plants which have a height of 5-15 cm are sprayed with the preparation of the active compound in such a way as to apply the particular amounts of active compound desired per unit area.
  • the concentration of the spray liquor is so chosen that the particular amounts of active compound desired are applied in 1,000 l of water/ha.
  • the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control.
  • the figures denote: ##EQU3##
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • Seeds of the test plants are sown in normal soil and, after 24 hours, watered with the preparation of the active compound. It is expedient to keep constant the amount of water per unit area.
  • the concentration of the active compound in the preparation is of no importance, only the amount of active compound applied per unit area being decisive.
  • the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control.
  • the figures denote: ##EQU4##

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Abstract

7Herbicidal 5-alkoxy-1,2,4-triazol-3-(thi)ones of the gerneral formula <IMAGE> (I) (in which the radicals R1, R2, R3, X and Y have the meanings given in the description), processes for their preparation, and their use as herbicides, and also new intermediates of the formula (II) <IMAGE> (II)

Description

This application is a continuation-in-part of application Ser. No. 07/976,185, filed Nov. 6, 1992, now U.S. Pat. No. 5,356,865, which in turn is a continuation-in-part of application Ser. No. 07/757,785, filed Nov. 11, 1991, now abandoned and is a continuation-in-part of application Ser. No. 08/048,026, filed Apr. 15, 1993, now abandoned, which in turn is a continuation-in-part of application Ser. No. 07/857,025, filed on Mar. 24, 1992, now abandoned, and this application further is a continuation-in-part of application Ser. No. 08/031,426, filed Mar. 15, 1993, now U.S. Pat. No. 5,405,970, which is a division of application Ser. No. 07/816,365, filed Dec. 30, 1991, now U.S. Pat. No. 5,241,074, which is a division of application Ser. No. 07/692,439, filed Apr. 29, 1991, now U.S. Pat. No. 5,094,683, which is a division of application Ser. No. 07/556,052, filed on Jul. 20, 1990 now U.S. Pat. No. 5,057,144, which is a continuation-in-part of Application Ser. No. 07/337,775, filed on Apr. 13, 1989, now abandoned.
The invention relates to new substituted 5-alkoxy-1,2,4-triazol-3-(thi)ones, a plurality of several processes, and also new intermediates for their preparation, and their use as herbicides.
This invention also relates to intermediates used to prepare new sulphonylaminocarbonyltriazolinones having substituents bonded via oxygen which possess herbicidal activity. The final products are disclosed in application Ser. No. 08/048,026, filed Apr. 15, 1993 incorporated herein by reference.
It has been disclosed that certain substituted triazolones such as, for example, 4-amino-5-methyl-2-phenylaminocarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-one, have herbicidal properties (cf. EP-A 283,876, EP-A 294,666, EP-A 298,371). However, the herbicidal activity of these compounds is not entirely satisfactory in all fields of application.
Further sulphonylaminocarbonyltriazolinones such as, for example, 2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one are the subject of an earlier, but non-prior-published Patent Application (cf. German Patent 3,934,081 dated Dec. 10, 1989).
New substituted 5-alkoxy-1,2,4-triazol-3-(thi)ones of the general formula (I) ##STR3## in which R1 represents alkyl, alkenyl, alkinyl, halogenoalkyl, halogenoalkenyl, halogenoalkinyl, cyanoalkyl, hydroxyalkyl, alkoxyalkyl, alkoximinoalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkenyl, alkylaminoalkyl or dialkylaminoalkyl, or represents in each case optionally substituted cycloalkyl, cycloalkylalkyl, cycloalkenyl or cycloalkenylalkyl, or represents optionally substituted heterocyclylalkyl, or represents alkoxy, alkenyloxy or alkinyloxy, or represents in each case optionally substituted aralkyl, aryloxyalkyl, aralalkenyl, arylalkinyl, aroyl, aryl, aralkyloxy or aryloxy.
R2 represents alkyl, alkenyl, alkinyl, halogenoalkyl, halogenoalkenyl, halogenoalkinyl, alkoxyalkyl, cyanoalkyl, alkoxy, cycloalkyl or cycloalkylalkyl,
R3 represents alkyl, alkenyl, alkinyl, halogenoalkyl, halogenoalkenyl, halogenoalkinyl, alkoxyalkyl or cyanoalkyl,
X represents oxygen or sulphur and
Y represents oxygen or sulphur, have now been found.
Furthermore, it has been found that the new substituted 5-alkoxy-1,2,4-triazol-3-(thi)ones of the general formula (I) are obtained when
(a) 5-alkoxy-1,2,4-triazol-3-(thi)ones of the general formula (II) ##STR4## in which R2, R3 and Y have the abovementioned meaning, are reacted with iso(thio)cyanates of the general formula (III)
R.sup.1 --N═C═X                                    (III)
in which
R1 and X have the abovementioned meanings, if appropriate in the presence of a diluent and if appropriate in the presence of a basic reaction auxiliary, or when
(b) 5-alkoxy-1,2,4-triazol-3-(thi)ones of the general formula (II) ##STR5## in which R2, R3 and Y have the abovementioned meaning are reacted with reactive (thio-)carbamates of the general formula (IV) ##STR6## in which R1 and X have the abovementioned meanings and
R4 represents alkyl, aralkyl or aryl, if appropriate in the presence of a diluent and if appropriate in the presence of a basic reaction auxiliary, or when
(c) 5-alkoxy-1,2,4-triazol-3-(thi)one derivatives of the general formula (V) ##STR7## in which R2, R3, X and Y have the abovementioned meanings and
R4 represents alkyl, aralkyl or aryl, are reacted with amino compounds of the general formula (VI)
R.sup.1 --NH.sub.2                                         (VI)
in which
R1 has the abovementioned meaning, if appropriate in the presence of a diluent and if appropriate in the presence of a basic reaction auxiliary.
Finally, it has been found that the new substituted 5-alkoxy-1,2,4-triazol-3-(thi)ones of the general formula (I) are distinguished by powerful herbicidal activity.
Surprisingly, the new compounds of the formula (I) show a considerably better herbicidal activity than the compound 4-amino-5-methyl-2-phenylaminocarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-one, which is known.
Additionally, there have been found novel sulphonylaminocarbonyltriazolinones having substitutuents bonded via oxygen, of the general formula (X) ##STR8## in which R2 represents hydrogen, amino, or an optionally substituted radical from the series comprising alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aryl, alkylamino, cycloalkylamino, dialkylamino,
R3 represents an optionally substituted radical from the series comprising alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, aralkyl, aryl, and
Ra represents an optionally substituted radical from the series comprising alkyl, aralkyl, aryl, heteroaryl,
and salts of compounds of the formula (X), with the exception of 2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one (cf. German Patent 3,934,081).
Formula (I) provides a general definition of the substituted 5-alkoxy-1,2,4-triazol-3-(thi)ones according to the invention. Preferred compounds of the formula (I) are those in which
R1 represents in each case straight-chain or branched alkyl having 1 to 18 carbon atoms, alkenyl having 2 to 8 carbon atoms, alkinyl having 2 to 8 carbon atoms, halogenoalkyl having 1 to 8 carbon atoms and 1 to 17 identical or different halogen atoms, halogenoalkenyl or halogenoalkinyl, each of which has 2 to 8 carbon atoms and 1 to 15 or 13 identical or different halogen atoms, cyanoalkyl having 1 to 8 carbon atoms, hydroxyalkyl having 1 to 8 carbon atoms and 1 to 6 hydroxyl groups, alkoxyalkyl, alkoximinoalkyl, alkoxycarbonylalkyl or alkoxycarbonylalkenyl, each of which has up to 6 carbon atoms in the individual alkyl or alkenyl moieties, alkylaminoalkyl or dialkylaminoalkyl, each of which has 1 to 6 carbon atoms in the individual alkyl moieties, or represents cycloalkyl, cycloalkylalkyl, cycloalkenyl or cycloalkenylalkyl, each of which has 3 to 8 carbon atoms in the cycloalkyl or cycloalkenyl moiety and if appropriate 1 to 6 carbon atoms in the alkyl moiety and each of which is optionally monosubstituted or polysubstituted by identical or different substituents, the following being selected as preferred substituents in the cyclic and optionally in the aliphatic moiety: halogen, cyano, and in each case straight-chain or branched alkyl or halogenoalkyl, each of which has 1 to 4 carbon atoms and if appropriate 1 to 9 identical or different halogen atoms, or in each case divalent alkanediyl or alkenediyl, each of which has up to 4 carbon atoms; R1 furthermore represents heterocyclylalkyl which has 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety and 1 to 9 carbon atoms as well as 1 to 3 hetero atoms--in particular nitrogen, oxygen and/or sulphur--in the heterocyclyl moiety and each of which is optionally monosubstituted or polysubstituted by identical or different substituents, the following being selected as preferred substituents: halogen, cyano, nitro, and in each case straight-chain or branched alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogenoalkylthio or alkoxycarbonyl, each of which has 1 to 5 carbon atoms and if appropriate 1 to 9 identical or different halogen atoms; R1 furthermore represents in each case straight-chain or branched alkoxy having 1 to 8 carbon atoms, alkenyloxy having 2 to 8 carbon atoms or alkinyloxy having 2 to 8 carbon atoms, and finally represents aralkyl, aryloxyalkyl, arylalkenyl, arylakinyl, aralkyloxy, aryloxy, aroyl or aryl, each of which has 6 or 10 carbon atoms in the aryl moiety and if appropriate up to 8 carbon atoms in the alkyl, alkenyl or alkinyl moiety, and each of which is optionally monosubstituted or polysubstituted by identical or different substituents, suitable aryl substituents in each case being: halogen, cyano, nitro, hydroxyl, in each case straight-chain or branched alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogenoalkylthio, alkylsulphinyl, alkylsulphonyl, halogenoalkylsulphinyl, halogenoalkylsulphonyl, alkanoyl or alkoxycarbonyl, each of which has 1 to 6 carbon atoms and if appropriate 1 to 9 identical or different halogen atoms, cycloalkyl having 3 to 6 carbon atoms and phenoxy, and suitable optional alkyl substituents being: halogen or cyano,
R2 represents in each case straight-chain or branched alkyl having 1 to 8 carbon atoms, alkenyl having 2 to 8 carbon atoms, alkinyl having 2 to 8 carbon atoms, halogenoalkyl having 1 to 8 carbon atoms and 1 to 17 identical or different halogen atoms, halogenoalkenyl having 2 to 8 carbon atoms and 1 to 15 identical or different halogen atoms, halogenoalkinyl having 2 to 8 carbon atoms and 1 to 13 identical or different halogen atoms, alkoxyalkyl or alkoxy, each of which has 1 to 6 carbon atoms in the individual alkyl moieties, cyanoalkyl having 1 to 8 carbon atoms, or represents cycloalkylalkyl or cycloalkyl, each of which has 3 to 7 carbon atoms in the cycloalkyl moiety and if appropriate 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety,
R3 represents in each case straight-chain or branched alkyl having 1 to 8 carbon atoms, alkenyl having 2 to 8 carbon atoms, alkinyl having 2 to 8 carbon atoms, halogenoalkyl having 1 to 8 carbon atoms and 1 to 17 identical or different halogen atoms, halogenoalkenyl having 2 to 8 carbon atoms and 1 to 15 identical or different halogen atoms, halogenoalkinyl having 2 to 8 carbon atoms and 1 to 13 identical or different halogen atoms, alkoxyalkyl having 1 to 6 carbon atoms in each of the individual alkyl moieties, or represents cyanoalkyl having 1 to 8 carbon atoms,
X represents oxygen or sulphur and
Y represents oxygen or sulphur and halogen in the substitution patterns mentioned in the case of R1, R2 and R3 represents fluorine, chlorine, bromine and iodine.
Particularly preferred compounds of the formula (I) are those in which
R1 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, in each case straight-chain or branched pentyl, hexyl, heptyl, octyl, nonyl, decyl or dodecyl, or represents allyl, propenyl, n- or i-butenyl, n- or i-pentenyl, n- or i-hexenyl, propargyl, n- or i-butinyl, n- or i-pentinyl, n- or i-hexinyl, or represents straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in particular fluorine, chlorine or bromine, or represents in each case straight-chain or branched halogenoalkenyl or halogenoalkinyl, each of which has 3 to 5 carbon atoms and 1 to 3 halogen atoms, in particular fluorine or chlorine, or represents in each case straight-chain or branched cyanoalkyl having 1 to 4 carbon atoms in the alkyl moiety, hydroxyalkyl having 1 to 6 carbon atoms and 1 to 3 hydroxyl groups, alkoxyalkyl, alkoximinoalkyl, alkoxycarbonylalkyl or alkoxycarbonylalkenyl, alkylaminoalkyl or dialkylaminoalkyl, each of which has up to 4 carbon atoms in the individual alkyl or alkenyl moieties, or represents cyclopropyl, cyclopropylmethyl, cyclopropylethyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopentylmethyl, cyclohexylmethyl, cyclohexylethyl, cyclohexenyl or cyclohexenylmethyl, each of which is optionally monosubstituted to trisubstituted by identical or different substituents, the following being selected as particularly preferred substituents in the cyclic and if appropriate in the aliphatic moiety: fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyano, methanediyl, ethanediyl, butanediyl or butadienediyl; R1 furthermore represents heterocyclylinethyl, heterocyclylethyl or heterocyclylpropyl, each of which is optionally monosubstituted to trisubstituted in the heterocyclyl moiety by identical or different substituents, suitable heterocycles in each case being: ##STR9## where Z in each case represents oxygen or sulphur and where the following are selected as particularly preferred substituents:
fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, methylthio, trifluoromethyl, trifluoromethoxy or trifluoromethylthio; R1 furthermore represents in each case straight-chain or branched alkoxy having 1 to 6 carbon atoms, alkenyloxy having 3 to 6 carbon atoms or alkinyloxy having 3 to 6 carbon atoms, or represents benzyl, phenylethyl, phenylpropyl, phenylbutyl, phenylpentyl, phenylhexyl, phenylheptyl, phenylcyanomethyl, phenylcyanoethyl, phenylcyanopropyl, phenoxymethyl, phenoxyethyl, phenoxypropyl, phenoxybutyl, phenylethinyl, benzyloxy, phenylethyloxy, phenoxy, benzoyl, phenyl or naphthyl, if appropriate straight-chain or branched, each of which is optionally monosubstituted to trisubstituted by identical or different substituents, suitable phenyl substituents in each case being: fluorine, chlorine, bromine, hydroxyl, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, methylthio, trifluoromethyl, difluoromethoxy, trifluoromethoxy, trifluoromethylthio, trifluoromethylsulphinyl, trifluoromethylsulphonyl, methylsulphinyl, methylsulphonyl, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, cyclohexyl and phenoxy,
R2 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n- or i-pentyl, n- or i-hexyl, or represents allyl, propargyl, methoxy, ethoxy, methoxymethyl, ethoxymethyl, methoxyethyl or ethoxyethyl, or represents straight-chain or branched halogenoalkyl, halogenoalkenyl and halogenoalkinyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in particular fluorine, chlorine or bromine, or represents cyclopentyl, cyclohexyl, cyclopropyl, cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl or cyclohexylethyl,
R3 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, n- or i-hexyl, or represents allyl, propargyl, methoxyethyl, ethoxyethyl, fluoroethyl, chloroethyl, fluoropropyl, chloropropyl or cyanoethyl,
X represents oxygen or sulphur and
Y represents oxygen or sulphur.
Very particularly preferred compounds of the formula (I) are those in which
R1 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, n-, i-, s- or t-hexyl, propargyl, n- or i-butinyl, n- or i-pentinyl, or represents straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 4 identical or different halogen atoms, in particular fluorine and chlorine, or represents cyanomethyl, cyanoethyl or n- or i-cyanopropyl, or represents cyclopropyl, cyclopropylmethyl, cyclopentyl, cyclopentylmethyl, cyclohexyl or cyclohexylmethyl, each of which is optionally monosubstituted to trisubstituted by identical or different substituents, or represents phenyl, benzyl or phenylethyl, each of which is optionally monosubstituted to trisubstituted by identical or different substituents from the series comprising fluorine, chlorine, bromine, methyl, ethyl and/or trifluoromethyl, or represents in each case straight-chain or branched phenylpropyl, phenylbutyl, phenylpentyl or phenylhexyl, or represents morpholinyl-C1 -C4 -alkyl,
R2 represents methyl, ethyl, n-, i- or cyclopropyl, n-, i-, s- or t-butyl,
R3 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n- or i-pentyl,
X represents oxygen and
Y represents oxygen.
The new sulphonylaminocarbonyltriazolinones having substituents bonded via oxygen, of the general formula (X), are obtained when
(a) triazolinones of the general formula (II) ##STR10## in which R2 and R3 have the abovementioned meanings are reacted with sulphonyl isocyanates of the general formula (XI)
R.sup.a --SO.sub.2 --N═C═O                         (XI)
in which
Ra has the abovementioned meaning, if appropriate in the presence of a diluent, or when
(b) triazolinone derivatives of the general formula (XII) ##STR11## in which R2 and R3 have the abovementioned meanings and
Z1 represents halogen, alkoxy, aralkoxy or aryloxy, are reacted with sulphonamides of the general formula (XIII)
R.sup.3 --SO.sub.2 --NH.sub.2                              (XIII)
in which
Ra has the abovementioned meaning, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent, or when
(c) triazolinones of the general formula (II) ##STR12## in which R2 and R3 have the abovementioned meanings are reacted with sulphonamide derivatives of the general formula (XIV)
R.sup.a --SO.sub.2 --NH--CO--Z                             (XIV)
in which
Ra has the abovementioned meaning and
Z1 represents halogen, alkoxy, aralkoxy or aryloxy, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent and, if appropriate, salts are formed, by customary methods, of the compounds of the formula (I) which have been prepared by process (a), (b) or (c).
The new sulphonylaminocarbonyltriazolinones having substituents bonded via oxygen, of the general formula (I), and their salts are distinguished by a powerful herbicidal activity.
Surprisingly, the new compounds of the formula (X) show a considerably better herbicidal action than the known compound 2-(2-chlorophenylsulphonylaminocarbonyl)-4,5-dimethyl-2,4-dihydro-3H-1,2,4-triazol-3-one, which has a similar structure.
The invention preferably relates to compounds of the formula (X) in which
R2 represents hydrogen, amino, or represents C1 -C6 -alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, C1 -C4 -alkoxy, C1 -C4 -alkylcarbonyl or C1 -C4 -alkoxy-carbonyl, or represents C3 -C6 -alkenyl or C3 C6 -alkinyl, each of which is optionally substituted by fluorine, chlorine and/or bromine, or represents C3 -C6 -cycloalkyl which is optionally substituted by fluorine, chlorine, bromine and/or C1 -C4 -alkyl, or represents phenyl-C1 -C3 -alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C1 -C4 -alkyl, trifluoromethyl, C1 -C4 -alkoxy and/or C1 -C4 -alkoxy-carbonyl, or represents phenyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C1 -C4 -alkyl, trifluoromethyl, C1 -C4 -alkoxy, fluorine- and/or chlorine-substituted C1 -C3 -alkoxy, C1 -C4 -alkylthio, fluorine- and/or chlorine-substituted C1 -C3 -alkylthio, C1 -C4 -alkylsulphinyl, C1 -C4 -alkylsulphonyl and/or C1 -C4 -alkoxycarbonyl, or represents C1 -C4 -alkylamino which is optionally substituted by fluorine, cyano, C1 -C4 -alkoxy or C1 -C4 -alkoxy-carbonyl, or represents C3 -C6 -cycloalkylamino or di-(C1 -C4 -alkyl)-amino,
R3 represents C1 -C6 -alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, C3 -C6 -cycloalkyl, C1 -C4 -alkoxy or C1 -C4 -alkoxycarbonyl, or represents C3 -C6 -alkenyl or C3 -C6 -alkinyl, each of which is optionally substituted by fluorine, chlorine and/or bromine, or represents C3 -C6 -cycloalkyl which is optionally substituted by fluorine, chlorine, bromine and/or C1 -C4 -alkyl, or represents cyclohexenyl, or represents phenyl-C1 -C3 -alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C1 -C4 -alkyl, trifluoromethyl, C1 -C4 -alkoxy and/or C1 -C4 -alkoxy-carbonyl, or represents phenyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C1 -C4 -alkyl, trifluoromethyl, C1 -C4 -alkoxy, fluorine- and/or chlorine-substituted C1 -C3 -alkoxy, C1 -C4 -alkylthio, fluorine- and/or chlorine-substituted C1 -C3 -alkylthio, C1 -C4 -alkyl-sulphinyl, C1 -C4 -alkylsulphonyl and/or C1 -C4 -alkoxy-carbonyl, and
Ra represents the group ##STR13## in which R4.spsp.1 and R5 are identical or different and represent hydrogen, fluorine, chlorine, bromine, iodine, nitro, C1 -C6 -alkyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C1 -C4 -alkoxycarbonyl, C1 -C4 -alkylamino-carbonyl, di- (C1 -C4 -alkyl) amino-carbonyl, hydroxyl, C1 -C4 -alkoxy, formyloxy, C1 -C4 -alkyl-carbonyloxy, C1 -C4 -alkoxy-carbonyloxy, C1 -C4 -alkylamino-carbonyloxy, C1 -C4 -alkylthio, C1 -C4 -alkylsulphinyl, C1 -C4 -alkylsulphonyl, di- (C1 -C4 -alkyl)-aminosulphonyl, C3 -C6 -cycloalkyl or phenyl), or represent C2 -C6 -alkenyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, C1 -C4 -alkoxy-carbonyl, carboxyl or phenyl), or represent C2 -C6 -alkinyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, C1 -C4 -alkoxy-carbonyl, carboxyl or phenyl), or represent C1 -C4 -alkoxy (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C1 -C4 -alkoxy-carbonyl, C1 -C4 -alkoxy, C1 -C4 -alkylthio, C1 -C4 -alkylsulphinyl or C1 -C4 -alkylsulphonyl), or represent C1 -C4 -alkylthio (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C1 -C4 -alkoxy-carbonyl, C1 -C4 -alkylthio, C1 -C4 -alkylsulphinyl or C1 -C4 -alkylsulphonyl), or represent C3 -C6 -alkenyloxy (which is optionally substituted by fluorine, chlorine, bromine, cyano or C1 -C4 -alkoxy-carbonyl), or represent C2 -C6 -alkenylthio (which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C1 -C3 -alkylthio or C1 -C4 -alkoxycarbonyl), C3 -C6 -alkinyloxy, C3 -C6 -alkinylthio or the radical --S(O)p --R6 where
p represents the numbers 1 or 2 and
R6 represents C1 -C4 -alkyl (which is optionally substituted by fluorine, chlorine, bromine, cyano or C1 -C4 -alkoxy-carbonyl), C3 -C6 -alkenyl, C3 -C6 -alkinyl, C1 -C4 -alkoxy, C1 -C4 -alkoxy-C1 -C4 -alkylamino, C1 -C4 -alkylamino, di-(C1 -C4 -alkyl)-amino, phenyl or the radical --NHOR7 where
R7 represents C1 -C12 -alkyl (which is optionally substituted by fluorine, chlorine, cyano, C1 -C4 -alkoxy, C1 -C4 -alkylthio, C1 -C4 -alkylsulphinyl, C1 -C4 -alkylsulphonyl, C1 -C4 -alkyl-carbonyl, C1 -C4 -alkoxy-carbonyl, C1 -C4 -alkylamino-carbonyl or di-(C1 -C4 -alkyl)-amino-carbonyl), or represents C3 -C6 -alkenyl (which is optionally substituted by fluorine, chlorine or bromine),C3 -C6 -alkinyl, C3 -C6 -cycloalkyl, C3 -C6 -cycloalkyl-C1 -C2 -alkyl, phenyl-C1 -C2 -alkyl (which is optionally substituted by fluorine, chlorine, nitro, cyano, C1 -C4 -alkyl, C1 -C4 -alkoxy or C1 -C4 -alkoxy-carbonyl), or represents benzhydryl, or represents phenyl (which is optionally substituted by fluorine, chlorine, nitro, cyano, C1 -C4 -alkyl, trifluoromethyl, C1 -C4 -alkoxy, C1 -C2 -fluoroalkoxy, C1 -C4 -alkylthio, trifluoromethylthio or C1 -C4 -alkoxy-carbonyl),
R4.spsp.1 and/or R5 furthermore represent phenyl or phenoxy, or represent C1 -C4 -alkylcarbonylamino, C1 -C4 -alkoxy-carbonylamino, C1 -C4 -alkylamino-carbonyl-amino, di-(C1 -C4 -alkyl)-amino-carbonylamino, or the radical --CO--R8 where
R8 represents C1 -C6 -alkyl, C1 -C6 -alkoxy, C3 -C6 -cycloalkoxy, C3 -C6 -alkenyloxy, C1 -C4 -alkylthio, C1 -C4 -alkylamino, C1 -C4 -alkoxyamino, C1 -C4 -alkoxy-C1 -C4 -alkyl-amino or di-(C1 -C4 -alkyl)-amino (which are optionally substituted by fluorine and/or chlorine),
R4.spsp.1 and/or R5 furthermore represent trimethylsilyl, thiazolinyl, C1 -C4 -alkylsulphonyloxy, di-(C1 -C4 -alkyl)aminosulphonylamino or the radical --CH═N--R9 where
R9 represents C1 -C6 -alkyl which is optionally substituted by fluorine, chlorine, cyano, carboxyl, C1 -C4 -alkoxy, C1 -C4 -alkylthio, C1 -C4 -alkylsulphinyl or C1 -C4 -alkylsulphonyl, or represents benzyl which is optionally substituted by fluorine or chlorine, or represents C3 -C6 -alkenyl or C3 -C6 -alkinyl, each of which is optionally substituted by fluorine or chlorine, or represents phenyl which is optionally substituted by fluorine, chlorine, bromine, C1 -C4 -alkyl, C1 -C4 -alkoxy, trifluoromethyl, trifluoromethoxy or trifluoromethylthio, or represents optionally fluorine- and/or chlorine-substituted C1 -C6 -alkoxy, C3 -C6 -alkenoxy, C3 -C6 -alkinoxy or benzyloxy, or represents amino, C1 -C4 -alkylamino, di-(C1 -C4 -alkyl)-amino, phenylamino, C1 -C4 -alkyl-carbonyl-amino, C1 -C4 -alkoxycarbonylamino or C1 -C4 -alkyl-sulphonylamino, or represents phenylsulphonylamino which is optionally substituted by fluorine, chlorine, bromine or methyl,
furthermore
Ra represents the radical ##STR14## where R10 represents hydrogen or C1 -C4 -alkyl,
R11 and R12 are identical or different and represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, C1 -C4 -alkyl (which is optionally substituted by fluorine and/or chlorine), C1 -C4 -alkoxy (which is optionally substituted by fluorine and/or chlorine), carboxyl, C1 -C4 -alkoxy-carbonyl, dimethylaminocarbonyl, C1 -C4 -alkylsulphonyl or di-(C1 -C4 -alkyl) -aminosulphonyl;
furthermore
Ra represents the radical ##STR15## where R13 and R14 are identical or different and represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, C1 -C4 -alkyl (which is optionally substituted by fluorine and/or chlorine) or C1 -C4 -alkoxy (which is optionally substituted by fluorine and/or chlorine);
furthermore
Ra represents the radical ##STR16## where R15 and R16 are identical or different and represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, C1 -C4 -alkyl (which is optionally substituted by fluorine and/or chlorine), C1 -C4 -alkoxy (which is optionally substituted by fluorine and/or chlorine), or represent C1 -C4 -alkylthio, C1 -C4 -alkylsulphinyl or C1 -C4 -alkylsulphonyl (which are optionally substituted by fluorine and/or chlorine), or represent aminosulphonyl, mono-(C1 -C4 -alkyl)-aminosulphonyl, di-(C1 -C4 -alkyl)-aminosulphonyl or C1 -C4 -alkoxycarbonyl or dimethylaminocarbonyl;
furthermore
Ra represents the radical ##STR17## where R17 and R18 are identical or different and represent hydrogen, fluorine, chlorine, bromine, C1 -C4 -alkyl (which is optionally substituted by fluorine and/or bromine), C1 -C4 -alkoxy (which is optionally substituted by fluorine and/or chlorine), C1 -C4 -alkylthio, C1 -C4 -alkylsulphinyl or C1 -C4 -alkylsulphonyl (which are optionally substituted by fluorine and/or chlorine), or represent di-(C1 -C4 -alkyl)-aminosulphonyl;
furthermore
Ra represents the radical ##STR18## where R19 and R20 are identical or different and represent hydrogen, fluorine, chlorine, bromine, cyano, nitro, C1 -C4 -alkyl (which is optionally substituted by fluorine and/or chlorine), C1 -C4 -alkoxy (which is optionally substituted by fluorine and/or chlorine), C1 -C4 -alkylthio, C1 -C4 -alkylsulphinyl or C1 -C4 -alkylsulphonyl (which is optionally substituted by fluorine and/or chlorine), di-(C1 -C4 -alkyl)-amino-sulphonyl, C1 -C4 -alkoxy-carbonyl or dimethylaminocarbonyl, and
A represents oxygen, sulphur or the group N--Z1, where
Z1 represents hydrogen, C1 -C4 -alkyl (which is optionally substituted by fluorine, chlorine, bromine or cyano), C3 -C6 -cycloalkyl, benzyl, phenyl (which is optionally substituted by fluorine, chlorine, bromine or nitro), C1 -C4 -alkylcarbonyl, C1 -C4 -alkoxy-carbonyl or di-(C1 -C4 -alkyl) -aminocarbonyl;
furthermore
Ra represents the radical ##STR19## where R21 and R22 are identical or different and represent hydrogen, C1 -C4 -alkyl, halogen, C1 -C4 -alkoxycarbonyl, C1 -C4 -alkoxy or C1 -C4 -halogenoalkoxy,
Y1 represents sulphur or the group N--R23, where
R23 represents hydrogen or C1 -C4 -alkyl;
furthermore
Ra represents the radical ##STR20## where R24 represents hydrogen, C1 -C4 -alkyl, benzyl, pyridyl, quinolinyl or phenyl,
R25 represents hydrogen, halogen, cyano, nitro, C1 -C4 -alkyl (which is optionally substituted by fluorine and/or chlorine), C1 -C4 -alkoxy (which is optionally substituted by fluorine and/or chlorine), dioxolanyl or C1 -C4 -alkoxy-carbonyl and
R26 represents hydrogen, halogen or C1 -C4 -alkyl;
furthermore
Ra represents one of the groups listed below ##STR21##
The invention furthermore preferably relates to the sodium, potassium, magnesium, calcium, ammonium, C1 -C4 -alkyl-ammonium, di-(C1 -C4 -alkyl)-ammonium, tri-(C1 -C4 -alkyl)-ammonium, C5 - or C6 -cycloalkyl-ammonium and di-(C1 -C2 -alkyl) -benzyl-ammonium salts of compounds of the formula (I) in which R1, R2 and R3 have the meanings mentioned above as being preferred.
In particular, the invention relates to compounds of the formula (X) in which
R2 represents hydrogen, amino, C1 -C4 -alkyl which is optionally substituted by fluorine, cyano, methoxy or ethoxy, or represents allyl, C3 -C6 -cycloalkyl, benzyl, phenyl, C1 -C3 -alkylamino, C3 -C6 -cycloalkylamino or di-(C1 -C3 -alkyl) -amino,
R3 represents C1 -C4 -alkyl which is optionally substituted by fluorine and/or chlorine, methoxy or ethoxy, or represents C3 -C4 -alkenyl which is optionally substituted by fluorine and/or chlorine, or represents C3 -C6 -cycloalkyl, or represents benzyl which is optionally substituted by fluorine, chlorine and/or methyl, and
Ra represents the group ##STR22## where R4.spsp.1 represents fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy, 2-chloro-ethoxy, 2-methoxyethoxy, C1 -C3 -alkylthio, C1 -C3 -alkylsulphinyl, C1 -C3 -alkylsulphonyl, dimethylaminosulphonyl, diethylaminosulphonyl, N-methoxy-N-methylaminosulphonyl, methoxyaminosulphonyl, phenyl, phenoxy or C1 -C3 -alkoxy-carbonyl and
R5 represents hydrogen, fluorine, chlorine or bromine;
furthermore
Ra represents the radical ##STR23## where R10 represents hydrogen,
R11 represents fluorine, chlorine, bromine, methyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylsulphonyl or dimethylaminosulphonyl and
R12 represents hydrogen;
furthermore
Ra represents the radical ##STR24## where R represents C1 -C4 -alkyl, or represents the radical ##STR25## where R represents C1 -C4 -alkyl.
The abovementioned definitions of radicals, in general or mentioned in preferred ranges, can be combined with each other in any desired way, that is to say also between the particular preferred ranges.
Examples of the compounds of the formula (I) according to the invention are listed in Table 1 below. ##STR26##
              TABLE 1                                                     
______________________________________                                    
Examples of the compounds of the formula (I)                              
R.sup.1                R.sup.2                                            
                              R.sup.3                                     
                                     X   Y                                
______________________________________                                    
i-C.sub.3 H.sub.7      CH.sub.3                                           
                              CH.sub.3                                    
                                     O   O                                
CF.sub.3C(CH.sub.3).sub.2                                                 
                       CH.sub.3                                           
                              C.sub.2 H.sub.5                             
                                     O   O                                
FCH.sub.2C(CH.sub.3).sub.2                                                
                       CH.sub.3                                           
                              C.sub.2 H.sub.5                             
                                     O   O                                
C.sub.2 H.sub.5 C(CH.sub.3).sub.2                                         
                       CH.sub.3                                           
                              CH.sub.3                                    
                                     O   O                                
C.sub.3 H.sub.7C(CH.sub.3).sub.2                                          
                       CH.sub.3                                           
                              CH.sub.3                                    
                                     O   O                                
i-C.sub.3 H.sub.7C(CH.sub.3).sub.2                                        
                       CH.sub.3                                           
                              CH.sub.3                                    
                                     O   O                                
                       CH.sub.3                                           
                              CH.sub.3                                    
                                     O   O                                
 ##STR27##             CH.sub.3                                           
                              CH.sub.3                                    
                                     O   O                                
 ##STR28##             CH.sub.3                                           
                              CH.sub.3                                    
                                     O   O                                
 ##STR29##             CH.sub.3                                           
                              CH.sub.3                                    
                                     O   O                                
 ##STR30##             CH.sub.3                                           
                              CH.sub.3                                    
                                     O   O                                
 ##STR31##             CH.sub.3                                           
                              CH.sub.3                                    
                                     O   O                                
 ##STR32##             CH.sub.3                                           
                              C.sub.2 H.sub.5                             
                                     O   O                                
 ##STR33##             CH.sub.3                                           
                              CH.sub.3                                    
                                     O   O                                
______________________________________
If, for example, 5-ethoxy-4-ethyl-2,4-dihydro-3H-1,2,4-triazole-3-thione and isopropyl-isocyanate are used as starting substances, the course of the reaction of process (a) according to the invention can be illustrated by the following equation: ##STR34##
If, for example, 5-isopropoxy-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one and O-Methyl-N-tert.-butylthiocarbamate are used as starting substances, the course of the reaction of process (b) according to the invention can be illustrated by the following equation: ##STR35##
If, for example, 4-isopropyl-5-methoxy-2-phenoxycarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-one and cyclohexylamine are used as starting substances, the course of the reaction of process (c) according to the invention can be illustrated by the following equation: ##STR36##
Formula (II) provides a general definition of the 5-alkoxy-1,2,4-triazol-3-(thi)ones to be used as starting substances in processes (a) and (b) according to the invention for the preparation of compounds of the formula (I).
In formula (II), R2, R3 and Y preferably, or in particular, have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention as being preferred, or as particularly preferred, for R2, R3 and Y.
Examples of the compounds of formula X are listed in Table 2 below--cf. also the Preparation Examples ##STR37##
                                  TABLE 2                                 
__________________________________________________________________________
Examples of the compounds of the formula (X)                              
R.sup.2   R.sup.3    R.sup.a                                              
__________________________________________________________________________
          CH.sub.3                                                        
                      ##STR38##                                           
 ##STR39##                                                                
          CH.sub.3                                                        
                      ##STR40##                                           
CH.sub.3  C.sub.2 H.sub.5                                                 
                      ##STR41##                                           
CH.sub.3  CH.sub.2CHCH.sub.2                                              
                      ##STR42##                                           
CH.sub.3  CH.sub.3                                                        
                      ##STR43##                                           
CH.sub.3  CH.sub.3                                                        
                      ##STR44##                                           
CH.sub.3  C.sub.2 H.sub.5                                                 
                      ##STR45##                                           
CH.sub.3  C.sub.2 H.sub.5                                                 
                      ##STR46##                                           
CH.sub.3  C.sub.2 H.sub.5                                                 
                      ##STR47##                                           
C.sub.2 H.sub.5                                                           
          C.sub.2 H.sub.5                                                 
                      ##STR48##                                           
C.sub.2 H.sub.5                                                           
          C.sub.3 H.sub.7                                                 
                      ##STR49##                                           
 ##STR50##                                                                
          CH.sub.3                                                        
                      ##STR51##                                           
 ##STR52##                                                                
          C.sub.2 H.sub.5                                                 
                      ##STR53##                                           
 ##STR54##                                                                
          CH(CH.sub.3).sub.2                                              
                      ##STR55##                                           
CH.sub.3  CH(CH.sub.3).sub.2                                              
                      ##STR56##                                           
CH.sub.3  CH.sub.2CHCH.sub.2                                              
                      ##STR57##                                           
C.sub.2 H.sub.5                                                           
          CH.sub.3                                                        
                      ##STR58##                                           
C.sub.2 H.sub.5                                                           
          C.sub.2 H.sub.5                                                 
                      ##STR59##                                           
CH.sub.3  C.sub.2 H.sub.5                                                 
                      ##STR60##                                           
C.sub.2 H.sub.5                                                           
          C.sub.3 H.sub.7                                                 
                      ##STR61##                                           
CH.sub.2  C.sub.2 H.sub.5                                                 
                      ##STR62##                                           
 ##STR63##                                                                
          CH.sub.3                                                        
                      ##STR64##                                           
 ##STR65##                                                                
          C.sub.2 H.sub.5                                                 
                      ##STR66##                                           
 ##STR67##                                                                
          CH.sub.3                                                        
                      ##STR68##                                           
 ##STR69##                                                                
          C.sub.2 H.sub.5                                                 
                      ##STR70##                                           
 ##STR71##                                                                
          C.sub.3 H.sub.7 -n                                              
                      ##STR72##                                           
CH.sub.3  C.sub.2 H.sub.5                                                 
                      ##STR73##                                           
CH.sub.3  CH.sub.3                                                        
                      ##STR74##                                           
CH.sub.3  C.sub.2 H.sub.5                                                 
                      ##STR75##                                           
CH.sub.3                                                                  
           ##STR76##                                                      
                      ##STR77##                                           
CH.sub.3  C.sub.2 H.sub.5                                                 
                      ##STR78##                                           
 ##STR79##                                                                
          C.sub.2 H.sub.5                                                 
                      ##STR80##                                           
 ##STR81##                                                                
          CH.sub.3                                                        
                      ##STR82##                                           
CH.sub.3  CH.sub.3                                                        
                      ##STR83##                                           
CH.sub.3  C.sub.3 H.sub.7                                                 
                      ##STR84##                                           
C.sub.2 H.sub.5                                                           
          C.sub.2 H.sub.5                                                 
                      ##STR85##                                           
CH.sub.2CHCH.sub.2                                                        
          C.sub.2 H.sub.5                                                 
                      ##STR86##                                           
CH.sub.2CHCH.sub.2                                                        
          CH.sub.3                                                        
                      ##STR87##                                           
C.sub.2 H.sub.5                                                           
          CH.sub.3                                                        
                      ##STR88##                                           
C.sub.2 H.sub.5                                                           
          C.sub.2 H.sub.5                                                 
                      ##STR89##                                           
C.sub.3 H.sub.7                                                           
          CH.sub.2CHCH.sub.2                                              
                      ##STR90##                                           
CH.sub.3  CH.sub.3                                                        
                      ##STR91##                                           
 ##STR92##                                                                
          C.sub.2 H.sub.5                                                 
                      ##STR93##                                           
 ##STR94##                                                                
          C.sub.2 H.sub.5                                                 
                      ##STR95##                                           
C.sub.2 H.sub.5                                                           
          C.sub.2 H.sub.5                                                 
                      ##STR96##                                           
CH.sub.3  C.sub.2 H.sub.5                                                 
                      ##STR97##                                           
CH.sub.3  C.sub.3 H.sub.7                                                 
                      ##STR98##                                           
C.sub.3 H.sub.7                                                           
          CH.sub.3                                                        
                      ##STR99##                                           
C.sub.3 H.sub.7                                                           
          CH.sub.3                                                        
                      ##STR100##                                          
C.sub.3 H.sub.7                                                           
          C.sub.2 H.sub.5                                                 
                      ##STR101##                                          
C.sub.3 H.sub.7                                                           
          C.sub.2 H.sub.5                                                 
                      ##STR102##                                          
CH.sub.3  C.sub.2 H.sub.5                                                 
                      ##STR103##                                          
CH.sub.3  CH.sub.3                                                        
                      ##STR104##                                          
N(CH.sub.3).sub.2                                                         
          CH.sub.3                                                        
                      ##STR105##                                          
CH.sub.3  C.sub.2 H.sub.5                                                 
                      ##STR106##                                          
C.sub.2 H.sub.5                                                           
          C.sub.2 H.sub.5                                                 
                      ##STR107##                                          
 ##STR108##                                                               
          CH.sub.3                                                        
                      ##STR109##                                          
CH.sub.3  C.sub.2 H.sub.5                                                 
                      ##STR110##                                          
N(CH.sub.3).sub.2                                                         
          CH.sub.3                                                        
                      ##STR111##                                          
__________________________________________________________________________
If, for example, 2,6-difluoro-phenylsulphonyl isocyanate and 5-ethoxy-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one are used as starting substances, the course of the reaction in process (a) according to the invention can be outlined by the following equation: ##STR112##
If, for example, 2-methylthio-benzenesulphonamide and 2-chlorocarbonyl-4-dimethylamino-5-propyloxy-2,4-dihydro-3H-1,2,4-triazol-3-one are used as starting substances, the course of the reaction in process (b) according to the invention can be outlined by the following equation: ##STR113##
If, for example, N-methoxycarbonyl-2-methoxy-benzenesulphonamide and 5-methoxy-4-difluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one are used as starting substances, the course of the reaction in process (c) according to the invention can be outlined by the following equation: ##STR114##
Formula (II) provides a general definition of the triazolinones to be used as starting substances in processes (a) and (c) according to the invention for the preparation of compounds of the formula (X).
In formula (II), R2 and R3 preferably, or in particular, have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (X) according to the invention as being preferred, or particularly preferred, for R2 and R3.
Examples of the starting substances of the formula (II) are listed in Table 3 below. ##STR115##
              TABLE 2                                                     
______________________________________                                    
Examples of the starting substances of the                                
formula (II)                                                              
R.sup.2    R.sup.3       γ                                          
______________________________________                                    
CH.sub.3   CH.sub.3      O                                                
CH.sub.3   CH.sub.3      S                                                
CH.sub.3   C.sub.2 H.sub.5                                                
                         O                                                
CH.sub.3   C.sub.2 H.sub.5                                                
                         S                                                
CH.sub.3   C.sub.3 H.sub.7                                                
                         O                                                
CH.sub.3   C.sub.3 H.sub.7                                                
                         S                                                
CH.sub.3   CH(CH.sub.3).sub.2                                             
                         O                                                
CH.sub.3   CH(CH.sub.3).sub.2                                             
                         S                                                
CH.sub.3   --CH.sub.2 --CH═CH.sub.2                                   
                         S                                                
CH.sub.3   --CH.sub.2 --CH═CH.sub.2                                   
                         S                                                
C.sub.2 H.sub.5                                                           
           CH.sub.3      O                                                
C.sub.2 H.sub.5                                                           
           CH.sub.3      S                                                
C.sub.2 H.sub.5                                                           
           C.sub.2 H.sub.5                                                
                         O                                                
C.sub.2 H.sub.5                                                           
           C.sub.2 H.sub.5                                                
                         S                                                
C.sub.2 H.sub.5                                                           
           CH(CH.sub.3).sub.2                                             
                         O                                                
C.sub.2 H.sub.5                                                           
           --CH.sub.2 --CH═CH.sub.2                                   
                         O                                                
C.sub.2 H.sub.5                                                           
           CH(CH.sub.3).sub.2                                             
                         S                                                
C.sub.2 H.sub.5                                                           
           --CH.sub.2 --CH═CH.sub.2                                   
                         S                                                
______________________________________                                    

              TABLE 3                                                     
______________________________________                                    
Examples of the starting substances of the                                
formula (II)                                                              
R.sup.2           R.sup.3      Y                                          
______________________________________                                    
H                 CH.sub.3     O                                          
CH.sub.3          CH.sub.3     O                                          
C.sub.2 H.sub.5   CH.sub.3     O                                          
C.sub.3 H.sub.7   CH.sub.3     O                                          
CH(CH.sub.3).sub.2                                                        
                  CH.sub.3     O                                          
C.sub.4 H.sub.9   CH.sub.3     O                                          
 ##STR116##       CH.sub.3     O                                          
CH.sub.3                                                                  
                   ##STR117##  O                                          
CH.sub.3                                                                  
                   ##STR118##  O                                          
C.sub.3 H.sub.7   C.sub.2 H.sub.5                                         
                               O                                          
 ##STR119##       C.sub.2 H.sub.5                                         
                               O                                          
CH.sub.2CHCH.sub.2                                                        
                  C.sub.2 H.sub.5                                         
                               O                                          
CH.sub.2CHBrCH.sub.2 Br                                                   
                  C.sub.2 H.sub.5                                         
                               O                                          
 ##STR120##       C.sub.3 H.sub.7                                         
                               O                                          
 ##STR121##       CH.sub.2CHCH.sub.2                                      
                               O                                          
 ##STR122##       CH(CH.sub.3).sub.2                                      
                               O                                          
C.sub.3 H.sub.7   CH(CH.sub.3).sub.2                                      
                               O                                          
CH.sub.2CHCH.sub.2                                                        
                  C.sub.3 H.sub.7                                         
                               O                                          
C.sub.2 H.sub.5   C.sub.3 H.sub.7                                         
                               O                                          
C.sub.2 H.sub.5                                                           
                   ##STR123##  O                                          
C.sub.3 H.sub.7   C.sub.3 H.sub.7                                         
                               O                                          
______________________________________
The starting substances of the formula (II) are known in some cases (cf. J. Chem. Soc C 1967, 2700-2704; J. Heterocycl. Chem. 15 (1978), 377-384) subject of an earlier, but non-prior-published, Patent Application (cf. German Patent 4,030,063, dated
Those compounds of the general formula (II) in which Y represents oxygen and R2 and R3 have the abovementioned meanings are new and are a subject of the present patent application.
The new 5-alkoxy-1,2,4-triazol-3-ones (II, Y=O) are obtained when hydrazinoformic esters of the general formula (VII)
H.sub.2 N--NH--CO--O--R.sup.4                              (VII)
in which
R4 has the abovementioned meaning are reacted with alkyliminocarboxylic diesters of the general formula (VIII) ##STR124## in which R2 and R3 have the abovementioned meaning, if appropriate in the presence of a diluent such as, for example, o-dichlorobenzene, at temperatures between 0° C. and 200° C., preferably between 50° C. and 150° C. (cf. the Preparation Examples).
The starting substances of the formulae (VII) and (VIII) are known chemicals.
Formula (III) provides the general definition of the iso(thio)cyanates to be used as starting substances in process (a) according to the invention for the preparation of compounds of the formula (I).
In formula (III), R1 and X preferably, or in particular, have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention as being preferred, or as particularly preferred, for R1 and X.
The starting substances of the formula (III) are known chemicals for organic synthesis.
Formula (IV) provides a general definition of the reactive (thio)carbamates to be used as starting substances in process (b) according to the invention for the preparation of compounds of the formula (I).
In formula (IV), R1 and X preferably, or in particular, have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention as being preferred, or as particularly preferred, for R1 and X;
R4 preferably represents methyl, ethyl, phenyl or benzyl.
The starting substances of the formula (IV) are known chemicals for organic synthesis.
Formula (V) provides a general definition of the 5-alkoxy-1,2,4-triazol-3-(thi)one derivatives to be used as starting substances in process (c) according to the invention for the preparation of compounds of the formula (I).
In formula (V), R2, R3, X and Y preferably, or in particular, have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention as being preferred, or as particularly preferred, for R2, R3, X and Y;
R4 preferably represents methyl, ethyl, phenyl or benzyl.
The starting substances of the formula (V) were hitherto not known from the literature and are a subject of the present patent application.
The new 5-alkoxy-1,2,4-triazol-3-(thi)one derivatives of the general formula (V) are obtained when 5-alkoxy-1,2,4-triazol-3-(thi)ones of the general formula (II) ##STR125## in which R2, R3 and Y have the abovementioned meanings are reacted with chloro(thio)formic esters of the general formula (IX) ##STR126## in which R4 and X have the abovementioned meanings, if appropriate in the presence of a diluent such as, for example, tetrahydrofuran, and if appropriate in the presence of an acid acceptor such as, for example, potassium tert-butylate, at temperatures between -20° C. and +100° C.
Formula (VI) provides a general definition of the amino compounds furthermore to be used as starting substances in process (c) according to the invention for the preparation of compounds of the formula (I).
In formula (VI), R1 preferably, or in particular, has the meaning which has already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention as being preferred, or as particularly preferred, for R1.
The starting substances of the formula (VI) are known chemicals for organic synthesis.
Processes (a), (b) and (c) according to the invention for the preparation of the new compounds of the formula (I) are preferably carried out in each case using diluents. Suitable diluents for this purpose are virtually all inert organic solvents. These preferably include aliphatic and aromatic, optionally halogenated hydrocarbons such as pentane, hexane, heptane, cyclohexane, petroleum ether, benzine, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, ethers such as diethyl ether and dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane, ketones such as acetone, methyl ethyl ketone, methyl isopropyl ketone and methyl isobutyl ketone, esters such as methyl acetate and ethyl acetate, nitriles such as, for example, acetonitrile and propionitrile, amides such as, for example, dimethylformamide, dimethylacetamide and N-methyl-pyrrolidone, and also dimethyl sulphoxide, tetramethylene sulphone and hexamethylphosphoric triamide.
If appropriate, processes (a), (b) and (c) according to the invention are in each case carried out in the presence of a basic reaction auxiliary. Suitable substances which are employed are preferably basic organic nitrogen compounds. These include, for example, trimethylamine, triethylamine, tripropylamine, tributylamine, diisopropylamine, dicyclohexylamine, N,N-dimethylaniline, N,N-dimethylbenzylamine, pyridine, 4-dimethylamino-pyridine, 1,5-diazabicyclo-(4,3,0]-non-5-ene (DBN), 1,8-diazabicyclo[5,4,0)-undec-7-ene (DBU) and 1,4-diazabicyclo-[2,2,2]-octane (DABCO).
When carrying out processes (a), (b) and (c) according to the invention, the reaction temperatures can be varied in each case in a substantial range. In general, the processes are carried out at temperatures between -20° C. and 150° C., preferably at temperatures between 0° C. and 100° C.
In general, processes (a), (b) and (c) according to the invention are carried out under atmospheric pressure. However, it is also possible to carry out the processes under increased or reduced pressure.
For carrying out processes (a), (b) and (c) according to the invention, the starting substances required in each case are generally employed in approximately equimolar amounts. However, it is also possible to use one of the two components employed in each case in a larger excess. In general, the reactions are carried out in a suitable diluent in the presence of a basic reaction auxiliary, and the reaction mixture is stirred for several hours at the particular temperature required. Working-up in the processes according to the invention is carried out in each case by customary methods.
The compounds of the general formula (II) which are used to prepare components of formula X in which R2 has the abovementioned meaning and R3 represents in each case optionally substituted cycloalkyl, cycloalkenyl, aralkyl or aryl, are new and a subject of the present patent application.
The compounds of the formula (II) are obtained when hydrazinoformic esters of the general formula (XV)
H.sub.2 N--NH--CO--O--R.sup.4.spsp.1                       (XV)
in which
R4.spsp.1 has the abovementioned meaning are reacted with alkyliminocarbonic diesters of the general formula (XVI) ##STR127## in which R2 and R3 have the abovementioned meaning, if appropriate in the presence of a diluent such as, for example, methanol, at temperatures between 0° C. and 50° C., and the compounds formed in this process, of the general formula (XVII) ##STR128## in which R2, R3 and R4.spsp.1 have the abovementioned meaning, are, if appropriate, isolated by customary methods and heated to temperatures between 50° C. and 150° C., if appropriate in the presence of a diluent such as, for example, toluene, xylene or o-dichlorobenzene (cf. Preparation Examples).
The starting substances of the formulae (XV) and (XVI) are known chemicals.
The intermediates of the formula (XVII) are new compounds.
Formula (XI) provides a general definition of the sulphonyl isocyanates furthermore to be used as starting substances in process (a) according to the invention for the preparation of compounds of the formula (X).
In formula (XI), Ra preferably, or in particular, has that meaning which has already been mentioned above in connection with the description of the compounds of the formula (X) according to the invention as being preferred, or particularly preferred, for Ra.
Examples of the starting substances of the formula (XI) which may be mentioned are: 2-fluoro-, 2-chloro-, 2-bromo-, 2-methyl-, 2-methoxy-, 2-trifluoromethyl-, 2-difluoro-methoxy-, 2-trifluoromethoxy-, 2-methylthio-, 2-ethylthio-, 2-propylthio-, 2-methylsulphinyl-, 2-methylsulphonyl-, 2-dimethylaminosulphonyl-, 2-diethylaminosulphonyl-, 2-(N-methoxy-N-methyl)-aminosulphonyl-, 2-phenyl-, 2-phenoxy-, 2-methoxycarbonyl-, 2-ethoxycarbonyl-, 2-propoxycarbonyl- and 2-isopropoxycarbonyl-phenylsulphonyl isocyanate, 2-fluoro-, 2-chloro-, 2-difluoromethoxy-, 2-trifluoromethoxy-, 2-methoxycarbonyl- and 2-ethoxycarbonyl-benzylsulphonyl isocyanate, 2-methoxycarbonyl-3-thienyl-sulphonyl isocyanate, 4-methoxycarbonyl- and 4-ethoxycarbonyl-1-methyl-pyrazol-5-yl-sulphonyl isocyanate.
The sulphonyl isocyanates of the formula (XI) are known and/or can be prepared by processes known per se (cf. U.S. Pat. Nos. 4,127,405, 4,169,719, 4,371,391; EP-A 7,687, 13,480, 21,641, 23,141, 23,422, 30,139, 35,893, 44,808, 44,809, 48,143, 51,466, 64,322, 70,041, 173,312).
Process (a) according to the invention for the preparation of the new compounds of the formula (X) is preferably carried out using diluents. Diluents which are suitable for this purpose are virtually all inert organic solvents. These preferably include aliphatic and aromatic, optionally halogenated hydrocarbons such as pentane, hexane, heptane, cyclohexane, petroleum ether, benzine, ligroine, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, ethers such as diethyl ether and dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane, ketones such as acetone, methyl ethyl ketone, methyl isopropyl ketone and methyl isobutyl ketone, esters such as methyl acetate and ethyl acetate, nitriles such as, for example, acetonitrile and propionitrile, amides such as, for example, dimethylformamide, dimethylacetamide and N-methylpyrrolidone, and also dimethyl sulphoxide, tetramethylene sulphone and hexamethylphosphoric triamide.
When carrying out process (a) according to the invention, the reaction temperatures can be varied within a substantial range. In general, the process is carried out at temperatures between 0° C. and 150° C., preferably at temperatures between 10° C. and 80° C.
In general, process (a) according to the invention is carried out under atmospheric pressure.
For carrying out process (a) according to the invention, between 1 and 3 moles, preferably between 1 and 2 moles, of sulphonyl isocyanate of the formula (XI) are generally employed per mole or triazolinone of the formula (II).
The reactants can be combined in any desired sequence. The reaction mixture is stirred until the reaction is complete and the product is isolated by filtration with suction. In another processing variant, the mixture is concentrated, and the crude product which remains in the residue is brought to crystallisation with a suitable solvent such as, for example, diethyl ether. The product of the formula (X) which is obtained in this way in crystalline form is isolated by filtration with suction.
Formula (XII) provides a general definition of the triazolinone derivatives to be used as starting substances in process (b) according to the invention for the preparation of compounds of the formula (X).
In formula (XII), R2 and R3 preferably, or in particular, have those meanings which have already been mentioned above in connection with description of the compounds of the formula (X) according to the invention as being preferred, or particularly preferred, for R2 and R3 and
Z1 preferably represents chlorine, C1 -C4 -alkoxy, benzyloxy or phenoxy, in particular methoxy or phenoxy.
Examples of the starting substances of the formula (XII) which are possible are the compounds of the formula (XII) which are to be prepared from the compounds of the formula (II) listed in Table 3 and phosgene, methyl chloroformate, benzyl chloroformate, phenyl chloroformate or diphenyl carbonate.
The starting substances of the formula XII were hitherto unknown.
The new triazolinone derivatives of the formula XII are obtained when triazolinones of the general formula (II) ##STR129## in which R2 and R3 have the abovementioned meanings are reacted with carbonic acid derivatives of the general formula (XVIII)
Z.sup.1 --CO--Z.sup.2                                      (XVIII)
in which
Z1 has the abovementioned meaning and
Z2 represents a leaving group such as chlorine, methoxy, benzyloxy or phenoxy,
if appropriate in the presence of a diluent such as, for example, tetrahydrofuran, and, if appropriate, in the presence of an acid acceptor such as, for example, sodium hydride or potassium tert-butylate, at temperatures between -20° C. and +100° C.
Formula (XVIII) provides a general definition of the sulphonamides furthermore to be used as starting substances in process (b) according to the invention for the preparation of compounds of the formula (X).
In formula (XIII), Ra preferably, or in particular, has that meaning which has already been mentioned above in connection with the description of the compounds of the formula (X) according to the invention as being preferred, or particularly preferred, for Ra.
The following may be mentioned as examples of the starting substances of the formula (XIII): 2-fluoro-, 2-chloro-, 2-bromo-, 2-methyl-, 2-methoxy-, 2-trifluoromethyl-, 2-difluoro-methoxy-, 2-trifluoromethoxy-, 2-methylthio-, 2-ethylthio-, 2-propylthio-, 2-methylsulphinyl-, 2-methylsulphonyl-, 2-dimethylaminosulphonyl-, 2-diethylaminosulphonyl-, 2-(N-methoxy-N-methyl)-aminosulphonyl-, 2-phenyl-, 2-phenoxy-, 2-methoxycarbonyl-, 2-ethoxycarbonyl-, 2-propoxycarbonyl- and 2-isopropoxycarbonyl-benzenesulphonamide, 2-fluoro-, 2-Chloro-, 2-difluoromethoxy-, 2-trifluoromethoxy-, 2-methoxycarbonyl- and 2-ethoxycarbonyl-phenylmethanesulphonamide, 2-methoxycarbonyl-3-thiophenesulphonamide, 4-methoxycarbonyl- and 4-ethoxycarbonyl-1-methyl-pyrazole-5-sulphonamide.
The sulphonamides of the formula (XIII) are known and/or can be prepared by processes known per se (cf. U.S. Pat. Nos. 4,127,405, 4,169,719, 4,371,391; EP-A 7,687, 13,480, 21,641, 23,141, 23,422, 30,139, 35,893, 44,808, 44,809, 48,143, 51,466, 64,322, 70,041, 173,312).
Process (b) according to the invention for the preparation of the new compounds of the formula (X) is preferably carried out using diluents. Diluents which are suitable for this purpose are virtually all inert organic solvents as have been indicated, for example, above in the case of process (a) according to the invention.
Acid acceptors which can be employed in process (b) according to the invention are all acid-binding agents which can customarily be employed for reactions of this type. The following are preferably suitable: alkali metal hydroxides such as, for example, sodium hydroxide and potassium hydroxide, alkaline earth metal hydroxides such as, for example, calcium hydroxide, alkali metal carbonates and alkali metal alcoholates such as sodium carbonate, potassium carbonate, sodium tert-butylate and potassium tert-butylate, furthermore aliphatic, aromatic or heterocyclic amines, for example triethylamine, trimethylamine, dimethylaniline, dimethylbenzylamine, pyridine, 1,5-diazabicyclo-[4.3.0]-non-5-ene (DBN), 1,8-diazabicyclo-[5.4.0]-undec-7-ene (DBU) and 1,4-diazabicyclo[2.2.2]-octane (DABCO).
When carrying out process (b) according to the invention, the reaction temperatures can be varied within a substantial range. In general, the process is carried out at temperatures between 0° C. and 100° C., preferably at temperatures between 10° C. and 60° C.
Process (b) according to the invention is generally carried out under atmospheric pressure. However, it can also be carried out under increased or reduced pressure.
For carrying out process (b) according to the invention, the starting substances required in each case are generally employed in approximately equimolar amounts. However, it is also possible to use one of the two components employed in each case in a larger excess. In general, the reactions are carried out in a suitable diluent in the presence of an acid acceptor, and the reaction mixture is stirred for several hours at the particular temperature required. Working-up in process (b) according to the invention is carried out in each case by customary methods.
The triazolinones of the formula (II) to be used as starting substances in process (c) according to the invention for the preparation of compounds of the formula (X) have already been described as starting substances for process (a) according to the invention.
Formula (XIV) provides a general definition of the sulphonamide derivatives furthermore to be used as starting substances in process (c) according to the invention for the preparation of compounds of the formula (X).
In formula (XIV), Ra and Z1 preferably, or in particular, have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (X) or (XII) according to the invention as being preferred, or particularly preferred, for Ra and Z1.
Process (c) according to the invention is preferably carried out using diluents. Solvents which are suitable for this purpose are the same organic solvents as have been mentioned above in connection with the description of process (a) according to the invention.
If appropriate, process (c) is carried out in the presence of an acid acceptor. Acid-binding agents which are suitable for this purpose are the same as have been mentioned above in connection with the description of process (b) according to the invention.
When carrying out process (c), the reaction temperatures can vary within a substantial range. In general, the process is carried out at temperatures between 0° C. and 100° C., preferably at temperatures between 10° C. and 60° C.
In general, process (c) according to the invention is carried out under atmospheric pressure. However, the process can also be carried out under increased or reduced pressure.
For carrying out process (c) according to the invention, the starting substances required in each case are generally employed in approximately equimolar amounts. However, it is also possible to use one of the two components employed in each case in a larger excess. The reactions are generally carried out in a suitable diluent in the presence of an acid acceptor, and the reaction mixture is stirred for several hours at the particular temperature required. Working-up is carried out in process (c) according to the invention in each case by customary methods.
To convert the compounds of the formula (X) into salts, they are stirred with suitable salt formers such as, for example, sodium hydroxide, sodium methylate, sodium ethylate, potassium hydroxide, potassium methylate or potassium ethylate, ammonia, isopropylamine, dibutylamine or triethylamine, in suitable diluents such as, for example, water, methanol or ethanol. The salts can be isolated in the form of crystalline products, if appropriate after concentration.
The active compounds according to the invention can be used as defoliants, desiccants, agents for destroying broad-leaved plants and, especially, as weed-killers. By weeds, in the broadest sense, there are to be understood all plants which grow in locations where they are undesired. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
The active compounds according to the invention can be used, for example, in connection with the following plants:
Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus and Taraxacum.
Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.
Monocotyledon weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus and Apera.
Monocotyledon cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium.
However, the use of the active compounds according to the invention is in no way restricted to these genera, but also extends in the same manner to other plants.
The compounds are suitable, depending on the concentration, for the total combating of weeds, for example on industrial terrain and rail tracks, and on paths and squares with or without tree plantings. Equally, the compounds can be employed for combating weeds in perennial cultures, for example afforestations, decorative tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and hopfields, on lawns, turf and pasture-land, and for the selective combating of weeds in annual cultures.
The compounds of the formula (I) according to the invention are suitable for selectively combating monocotyledon and dicotyledon weeds, mainly in monocotyledon cultures, by the pre- and the post-emergence method.
Some of the compounds of the formula (X) according to the invention are suitable for total or semi-total weed control, some for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon cultures, both pre-emergence and post-emergence.
The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with active compound, and very fine capsules in polymeric substances.
These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surface-active agents, that is emulsifying agents and/or dispersing agents and/or foam-forming agents.
In the case of the use of water as an extender, organic solvents can, for example, also be used as auxiliary solvents. As liquid solvents, there are suitable in the main: aromatics, such as xylene, toluene, or alkyl-naphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, as well as water.
As solid carriers there are suitable: for example ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as highly disperse silica, alumina and silicates, as solid carriers for granules there are suitable: for example crushed and fractionated natural minerals such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; as emulsifying and/or foam-forming agents there are suitable: for example non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates as well as albumen hydrolysis products; as dispersing agents there are suitable: for example lignin-sulphite waste liquors and methylcellulose.
Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latexes, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations. Further additives can be mineral and vegetable oils.
It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
The formulations in general contain between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%.
For combating weeds, the active compounds according to the invention, as such or in the form of their formulations, can also be used as mixtures with known herbicides, finished formulations or tank mixes being possible.
Suitable herbicides for the mixtures are known herbicides, such as, for example, 1-amino-6-ethylthio-3-(2,2-dimethylpropyl)-1,3,5-triazine-2,4(1H,3H)-dione (AMETHYDIONE) or N-(2-benzothiazolyl)-N,N'-dimethylurea (METABENZTHIAZURON) for combating weeds in cereals; 4-amino3-methyl-6-phenyl-1,2,4-triazin-5(4H)-one (METAMITRON) for combating weeds in sugar beet and 4-amino-6-(1,1-dimethylethyl)-3-methylthio-1,2,4-triazin-(4H) -one (METRIBUZIN) for combating weeds in soya beans; furthermore also 2,4-dichlorophenoxyacetic acid (2,4-D); 4-(2,4-dichlorophenoxy)-butyric acid (2,4-DB); 2,4-dichlorophenoxypropionic acid (2,4-DP); 2-chloro-2', 6'-diethyl-N-methoxy-methylacetanilide (ALACHLOR); methyl-6,6-dimethyl-2,4-dioxo-3-[1-(2-propenyloxyamino)-butylidene]-cyclohexanecarboxylic acid (ALLOXYDIM); 4-aminobenzenesulphonyl methyl carbamate (ASULAM); 2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine (ATRAZINE); methyl 2-[[[[[(4,6-dimethoxypyrimidin-2-yl)-amino]carbonyl]-amino]-sulphonyl]-methyl]-benzoate (BENSULFURON); 3-isopropyl-2,1,3-benzothiadiazin-4-one-2,2-dioxide (BENTAZONE); 3,5-dibromo-4-hydroxy-benzonitrile (BROMOXYNIL); N-(butoxymethyl)-2-chloro-N-(2,6-diethylphenyl)-acetamide (BUTACHLOR); 5-amino-4-chloro-2-phenyl-2,3-dihydro-3-oxy-pyridazine (CHLORIDAZONE); isopropyl N-(3-chlorophenyl)-carbamate (CHLORPROPHAM); 2-chloro-N-{[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-amino]-carbonyl}-benzenesulphonamide (CHLORSULFURON); N,N-dimethyl-N'-(3-chloro-4-methyl-phenyl)-urea (CHLORTOLURON); exo-1-methyl-4-(1-methyl-ethyl)-2-(2-methylphenyl-methoxy)-7-oxabicyclo-(2,2,1)-heptane (CINMETHYLIN); 3,6-dichloro-2-pyridinecarboxylic acid (CLOPYRALID); 2-chloro-4-ethylamino-6-(3-cyanopropylamino)-1,3,5-triazine (CYANAZINE); N,S-diethyl N-cyclohexyl-thiolcarbamate (CYCLOATE); 2-[1-(ethoximino)-butyl]-3-hydroxy-5-[tetrahydro-(2H)-thiopyran-3-yl]-2-cyclohexene-1-one (CYCLOXYDIM); 2-[4-(2,4-dichlorophenoxy)-phenoxy]-propionic acid, its methyl ester or its ethyl ester (DICLOFOP); 2-[(2-chlorophenyl)methyl]-4,4-dimethylisoxazolidin-3-one (DIMETHAZONE); S-ethyl N,N-di-n-propyl-thiocarbamidate (EPTAME); 4-amino-6-t-butyl-3-ethylthio-1,2,4-triazin-5(4H)-one (ETHIOZIN); 2-{4-[(6-chloro-2-benzoxazolyl)-oxy]phenoxy}-propanoic acid, its methyl ester or its ethyl ester (FENOXAPROP); 2-[4-(5-trifluoromethyl-2-pyridyloxy)-phenoxy]-propanoic acid or its butyl ester (FLUAZIFOP); 1-methyl-3-phenyl-5-(3-trifluoromethylphenyl)-4-pyridone (FLURIDONE); [(4-amino-3,5-dichloro-6-fluoro-2-pyridinyl)-oxy]-acetic acid or its 1-methylheptyl ester (FLUROXYPYR); 2-{4-[(3-chloro-5-(trifluoromethyl)-2-pyridinyl)-oxy]-phenoxy}-propanoic acid or its ethyl ester (HALOXYFOP); 3-cyclohexyl-6-dimethylamino-1-methyl-1,3,5-triazine-2,4-dione (HEXAZINONE); methyl 2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-4(5)-methylbenzoate (IMAZAMETHABENZ); 3,5-diiodo-4-hydroxybenzonitrile (IOXYNIL); N,N-dimethyl-N'-(4-isopropylphenyl)-urea (ISOPROTURON); (2-methyl-4-chlorophenoxy)-acetic acid (MCPA); (4-chloro-2-methylphenoxy)-propionic acid (MCPP); N-methyl-2-(1,3-benzothiazol-2-yloxy)-acetanilide (MEFENACET); 2-chloro-N-(2,6-dimethylphenyl)-N-[(1H)-pyrazol-1-yl-methyl]acetamide (METAZACHLOR); 2-ethyl-6-methyl-N-(1-methyl-2-methoxyethyl)-chloroacetanilide (METOLACHLOR); 2-{[[((4-methoxy-6-methyl-1,3,5-triazin-2-yl)-amino)carbonyl]-amino]-sulphonyl}-benzoic acid or its methyl ester (METSULFURON); S-ethyl N,N-hexamethylene-thiocarbamate (MOLINATE); 1-(3-trifluoromethylphenyl)-4-methylamino-5-chloro-6-pyridazone (NORFLURAZON); 4-(di-n-propyl-amino)-3,5-dinitrobenzenesulphonamide (ORYZALIN); N-(1-ethylpropyl)-3,4-dimethyl-2,6-dinitroaniline (PENDIMETHALIN); 3-(ethoxycarbonylaminophenyl)-N-(3'-methylphenyl)-carbamate (PHENMEDIPHAM); 2-chloro-N-isopropylacetanilide (PROPACHLOR); isopropyl N-phenyl-carbamate (PROPHAM); O-(6-chloro-3-phenyl-pyridazin-4-yl) S-octyl thiocarbonate (PYRIDATE); ethyl 2-[4-(6-chloroquinoxalin-2-yl-oxy)-phenoxy]-propionate (QUIZALOFOPETHYL); 2-[1-(ethoxamino)-butylidene]-5-(2-ethylthiopropyl)-1,3-cyclohexadione (SETHOXYDIM); 2-chloro-4,6-bis-(ethylamino)-1,3,5-triazine (SIMAZINE); 2,4-bis-[N-ethylamino]-6-methylthio-1,3,5-triazine (SIMETRYNE); 4-ethylamino-2-t-butylamino-6-methylthio-s-triazine (TERBUTRYNE); methyl 3-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-amino]-carbonyl]-amino]-sulphonyl]-thiophene-2-carboxylate (THIAMETURON); S-[(4-chlorophenyl)-methyl]N,N-diethylthiocarbamate (THIOBENCARB); S-(2,3,3-trichloroallyl) N,N-diisopropylthiocarbamate (TRIALLATE); 2,6-dinitro-4-trifluoromethyl-N,N-dipropylaniline (TRIFLURALIN). Surprisingly, some mixtures also show a synergistic action.
Mixtures with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, are also possible.
The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary manner, for example by watering, spraying, atomising or scattering.
The active compounds according to the invention can be applied either before or after emergence of the plants.
They can also be incorporated into the soil before sowing.
The amount of active compound used can vary within a substantial range. It depends essentially on the nature of the desired effect. In general, the amounts used are between 1 g and 10 kg of active compound per hectare of soil surface, preferably between 10 g and 5 kg per ha.
The preparation and use of the active compounds according to the invention can be seen from the following examples.
PREPARATION EXAMPLES Example 1 ##STR130##
A mixture of 1.3 g (0.01 mol) of 5-methoxy-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 0.1 g of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), 1.0 g (0.01 mol) of tertbutyl isocyanate and 50 ml of acetonitrile is stirred for 12 hours at 20° C. and subsequently concentrated under a water pump vacuum. The residue is taken up in methylene chloride, and the mixture is washed with water, dried with magnesium sulphate and filtered. The filtrate is concentrated under a water pump vacuum, the residue is brought to crystallisation by trituration with petroleum ether, and the product is isolated by filtration with suction.
1.4 g (61% Of theory) of 2-tert-butyl-amino-carbonyl-5-methoxy-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 167° C. are obtained.
Other examples of the compounds of the formula (I) which can be prepared analogously to Example 1 and corresponding to the general description of the preparation processes according to the invention are those listed in Table 4 below. ##STR131##
                                  TABLE 4                                 
__________________________________________________________________________
Preparation examples of the compounds of the formula (I)                  
Example                                           Melting                 
No.  R.sup.1                R.sup.2  R.sup.3  X Y point                   
__________________________________________________________________________
                                                  (°C.)            
 2                                                                        
                            CH.sub.3 CH.sub.3 O O 153                     
 3                                                                        
      ##STR132##            C.sub.3 H.sub.7                               
                                     CH.sub.3 O O (oil)                   
 4                                                                        
      ##STR133##            C.sub.3 H.sub.7                               
                                     CH.sub.3 O O (oil)                   
 5                                                                        
      ##STR134##            CH.sub.3 C.sub.2 H.sub.5                      
                                              O O (oil)                   
 6                                                                        
      ##STR135##            C.sub.2 H.sub.5                               
                                     CH.sub.3 O O (oil)                   
 7                                                                        
      ##STR136##            CH.sub.3 C.sub.2 H.sub.5                      
                                              O O (oil)                   
 8                                                                        
      ##STR137##            CH.sub.3 C.sub.2 H.sub.5                      
                                              O O (oil)                   
 9                                                                        
      ##STR138##            CH.sub.3 C.sub.2 H.sub.5                      
                                              O O (oil)                   
10                                                                        
      ##STR139##            CH.sub.3 C.sub.2 H.sub.5                      
                                              O O (oil)                   
11                                                                        
      ##STR140##            CH.sub.3 C.sub.2 H.sub.5                      
                                              O O (oil)                   
12                                                                        
      ##STR141##            CH.sub.3 C.sub.2 H.sub.5                      
                                              O O (oil)                   
13                                                                        
      ##STR142##            CH.sub.3 C.sub.2 H.sub.5                      
                                              O O (oil)                   
14                                                                        
      ##STR143##            CH.sub.3 CH.sub.3 O O 166                     
15                                                                        
      ##STR144##            CH.sub.3 CH.sub.3 O O 120                     
16                                                                        
      ##STR145##            CH.sub.3 CH.sub.3 O O 176                     
17                                                                        
      ##STR146##            CH.sub.3 CH.sub.3 O O 130                     
18                                                                        
      ##STR147##            CH.sub.3 CH.sub.3 O O 104                     
19                                                                        
      ##STR148##            CH.sub.3 CH.sub.3 O O 117                     
20                                                                        
      ##STR149##            CH.sub.3 CH.sub.3 O O 100                     
21   (CH.sub.3).sub.3 C     CH.sub.3 C.sub.3 H.sub.7                      
                                              O O  75                     
22                                                                        
      ##STR150##            CH.sub.3 C.sub.3 H.sub.7                      
                                              O O  95                     
23                                                                        
      ##STR151##            CH.sub.3 CH.sub.3 O O 142                     
24                                                                        
      ##STR152##            CH.sub.3 CH.sub.3 O O 135                     
25                                                                        
      ##STR153##            CH.sub.3 CH.sub.3 O O 106                     
26                                                                        
      ##STR154##            CH.sub.3 CH.sub.3 O O 137                     
27                                                                        
      ##STR155##            CH.sub.3 CH.sub.3 O O 131                     
28                                                                        
      ##STR156##            CH.sub.3 CH.sub.3 O O 118                     
29                                                                        
      ##STR157##            CH.sub.3 CH.sub.3 O O  82                     
30   (CH.sub.3).sub.3 C     CH.sub.2 CHCH.sub.2                           
                                     CH.sub.3 O O  87                     
31   (CH.sub.3).sub.3 C     n-C.sub.3 H.sub.7                             
                                     CH.sub.3 O O 144                     
32   (CH.sub.3).sub.3 C     CH.sub.3 C.sub.2 H.sub.5                      
                                              O O 102-103                 
33   (CH.sub.3).sub.3 C     CH.sub.3 C.sub.4 H.sub.9 -n                   
                                              O O 79-80                   
34   (CH.sub.3).sub.3 C                                                   
                             ##STR158##                                   
                                     C.sub.2 H.sub.5                      
                                              O O 108                     
35   (CH.sub.3).sub.3 C     C.sub.2 H.sub.5                               
                                     CH.sub.3 O O 144-146                 
36   (CH.sub.3).sub.3 C     CH.sub.2 CHCH.sub.2                           
                                     C.sub.2 H.sub.5                      
                                              O O 63-64                   
37   (CH.sub.3).sub.3 C     i-C.sub.3 H.sub.7                             
                                     C.sub.2 H.sub.5                      
                                              O O 68-69                   
38   (CH.sub.3).sub.3 C     (CH.sub.2).sub.3 OCH.sub.3                    
                                     CH.sub.3 O O 86-87                   
39   (CH.sub.3).sub.3 C     n-C.sub.3 H.sub.7                             
                                     C.sub.2 H.sub.5                      
                                              O O 70-71                   
40                                                                        
      ##STR159##            CH.sub.3 C.sub.4 H.sub.9 -n                   
                                              O O Oil                     
41                                                                        
      ##STR160##                                                          
                             ##STR161##                                   
                                     C.sub.2 H.sub.5                      
                                              O O Oil                     
42                                                                        
      ##STR162##            C.sub.2 H.sub.5                               
                                     CH.sub.3 O O Oil                     
43                                                                        
      ##STR163##            CH.sub.3 i-C.sub.3 H.sub.7                    
                                              O O Oil                     
44                                                                        
      ##STR164##            n-C.sub.3 H.sub.7                             
                                     CH.sub.3 O O  78                     
45                                                                        
      ##STR165##            CH.sub.2 CHCH.sub.2                           
                                     C.sub.2 H.sub.5                      
                                              O O Oil                     
46                                                                        
      ##STR166##            n-C.sub.3 H.sub.7                             
                                     CH.sub.3 O O 93-94                   
47                                                                        
      ##STR167##            CH.sub.3 C.sub.4 H.sub.9 -n                   
                                              O O Oil                     
48                                                                        
      ##STR168##                                                          
                             ##STR169##                                   
                                     C.sub.2 H.sub.5                      
                                              O O Oil                     
49                                                                        
      ##STR170##            C.sub.2 H.sub.5                               
                                     CH.sub.3 O O Oil                     
50                                                                        
      ##STR171##            CH.sub.2 CHCH.sub.2                           
                                     C.sub.2 H.sub.5                      
                                              O O Oil                     
51                                                                        
      ##STR172##            i-C.sub.3 H.sub.7                             
                                     C.sub.2 H.sub.5                      
                                              O O Oil                     
52                                                                        
      ##STR173##            (CH.sub.2).sub.3 OCH.sub.3                    
                                     CH.sub.3 O O 104-105                 
53                                                                        
      ##STR174##            n-C.sub.3 H.sub.7                             
                                     C.sub.2 H.sub.5                      
                                              0 0 Oil                     
54                                                                        
      ##STR175##            i-C.sub.3 H.sub.7                             
                                     CH.sub.3 O O Oil                     
55                                                                        
      ##STR176##            CH.sub.3 i-C.sub.3 H.sub.7                    
                                              O O Oil                     
56                                                                        
      ##STR177##            n-C.sub.3 H.sub.7                             
                                     CH.sub.3 O O Oil                     
57                                                                        
      ##STR178##            CH.sub.3 C.sub.2 H.sub.5                      
                                              O O Oil                     
58                                                                        
      ##STR179##            C.sub.2 H.sub.5                               
                                     CH.sub.3 O O Oil                     
59                                                                        
      ##STR180##            CH.sub.2 CHCH.sub.2                           
                                     C.sub.2 H.sub.5                      
                                              O O Oil                     
60                                                                        
      ##STR181##            n-C.sub.3 H.sub.7                             
                                     C.sub.2 H.sub.5                      
                                              O O Oil                     
61                                                                        
      ##STR182##            i-C.sub.3 H.sub.7                             
                                     CH.sub.3 O O Oil                     
62                                                                        
      ##STR183##            CH.sub.3 i-C.sub.3 H.sub.7                    
                                              O O Oil                     
63                                                                        
      ##STR184##            n-C.sub.3 H.sub.7                             
                                     CH.sub.3 O O Oil                     
64                                                                        
      ##STR185##            CH.sub.3 C.sub.2 H.sub.5                      
                                              O O Oil                     
65                                                                        
      ##STR186##            CH.sub.3 n-C.sub.4 H.sub.9                    
                                              O O Oil                     
66                                                                        
      ##STR187##            C.sub.2 H.sub.5                               
                                     CH.sub.3 O O Oil                     
67                                                                        
      ##STR188##            n-C.sub.3 H.sub.7                             
                                     C.sub.2 H.sub.5                      
                                              O O Oil                     
68                                                                        
      ##STR189##            i-C.sub.3 H.sub.7                             
                                     CH.sub.3 O O Oil                     
69                                                                        
      ##STR190##            n-C.sub.3 H.sub.7                             
                                     CH.sub.3 O O Oil                     
70                                                                        
      ##STR191##            CH.sub.3 C.sub.2 H.sub.5                      
                                              O O Oil                     
71                                                                        
      ##STR192##            CH.sub.3 n-C.sub.4 H.sub.9                    
                                              O O Oil                     
72                                                                        
      ##STR193##            C.sub.2 H.sub.5                               
                                     CH.sub.3 O O Oil                     
73                                                                        
      ##STR194##            n-C.sub.3 H.sub.7                             
                                     C.sub.2 H.sub.5                      
                                              O O Oil                     
74                                                                        
      ##STR195##            n-C.sub.3 H.sub.7                             
                                     CH.sub.3 O O Oil                     
75                                                                        
      ##STR196##            CH.sub.3 C.sub.2 H.sub.5                      
                                              O O Oil                     
76                                                                        
      ##STR197##            C.sub.2 H.sub.5                               
                                     CH.sub.3 O O Oil                     
77                                                                        
      ##STR198##            CH.sub.2 CHCH.sub.2                           
                                     C.sub.2 H.sub.5                      
                                              O O Oil                     
78                                                                        
      ##STR199##            n-C.sub.3 H.sub.7                             
                                     C.sub.2 H.sub.5                      
                                              O O Oil                     
79                                                                        
      ##STR200##            n-C.sub.3 H.sub.7                             
                                     CH.sub.3 O O 107-108                 
80                                                                        
      ##STR201##            CH.sub.3 C.sub.4 H.sub.9 -n                   
                                              O O Oil                     
81                                                                        
      ##STR202##            C.sub.2 H.sub.5                               
                                     CH.sub.3 O O 83-85                   
82                                                                        
      ##STR203##            n-C.sub.3 H.sub.7                             
                                     C.sub.2 H.sub.5                      
                                              O O 125-127                 
83                                                                        
      ##STR204##            i-C.sub.3 H.sub.7                             
                                     CH.sub.3 O O 108-110                 
84                                                                        
      ##STR205##            n-C.sub.3 H.sub.7                             
                                     CH.sub.3 O O 100-102                 
85                                                                        
      ##STR206##            CH.sub.3 C.sub.2 H.sub.5                      
                                              O O 164-166                 
86                                                                        
      ##STR207##            CH.sub.3 n-C.sub.4 H.sub.9                    
                                              O O 145                     
87                                                                        
      ##STR208##            n-C.sub.3 H.sub.7                             
                                     CH.sub.3 O O 109-110                 
88                                                                        
      ##STR209##                                                          
                             ##STR210##                                   
                                     C.sub.2 H.sub.5                      
                                              O O 123-125                 
89                                                                        
      ##STR211##            n-C.sub.3 H.sub.7                             
                                     C.sub.2 H.sub.5                      
                                              O O 95-98                   
90                                                                        
      ##STR212##            CH.sub.3 C.sub.2 H.sub.5                      
                                              O O 90-91                   
91                                                                        
      ##STR213##            CH.sub.3 C.sub.2 H.sub.5                      
                                              O O 64-66                   
92                                                                        
      ##STR214##            CH.sub.3 C.sub.2 H.sub.5                      
                                              O O 84-85                   
93                                                                        
      ##STR215##            CH.sub.3 C.sub.2 H.sub.5                      
                                              O O 104-105                 
94                                                                        
      ##STR216##            CH.sub.3 C.sub.2 H.sub.5                      
                                              O O 113-116                 
95                                                                        
      ##STR217##                                                          
                             ##STR218##                                   
                                     C.sub.2 H.sub.5                      
                                              O O  95                     
96                                                                        
      ##STR219##            CH.sub.3 C.sub.2 H.sub.5                      
                                              O O 115-116                 
97   (CH.sub.3).sub.3 C     CH.sub.3 i-C.sub.3 H.sub.7                    
                                              O O 82-84                   
98   ClCH.sub.2 C(CH.sub.3).sub.2                                         
                            n-C.sub.3 H.sub.7                             
                                     CH.sub.3 O O 93-95                   
99   ClCH.sub.2 C(CH.sub.3).sub.2                                         
                            CH.sub.3 n-C.sub.4 H.sub.9                    
                                              O O 85-87                   
100  ClCH.sub.2 C(CH.sub.3).sub.2                                         
                            C.sub.2 H.sub.5                               
                                     CH.sub.3 O O 127-129                 
101  ClCH.sub.2 C(CH.sub.3).sub.2                                         
                            CH.sub.2 CHCH.sub.2                           
                                     C.sub.2 H.sub.5                      
                                              O O Oil                     
102  ClCH.sub.2 C(CH.sub.3).sub.2                                         
                            n-C.sub.3 H.sub.7                             
                                     C.sub.2 H.sub.5                      
                                              O O 63-65                   
103  ClCH.sub.2 C(CH.sub.3).sub.2                                         
                            CH.sub.3 i-C.sub.3 H.sub.7                    
                                              O O 85-87                   
104  ClCH.sub.2 C(CH.sub.3).sub.2                                         
                            CH.sub.3 C.sub.2 H.sub.5                      
                                              O O 95-96                   
105                                                                       
      ##STR220##            CH.sub.3 i-C.sub.3 H.sub.7                    
                                              O O 146                     
106                                                                       
      ##STR221##            CH.sub.3 i-C.sub.3 H.sub.7                    
                                              O O Oil                     
107                                                                       
      ##STR222##            CH.sub.3 i-C.sub.3 H.sub.7                    
                                              O O Oil                     
108                                                                       
      ##STR223##            CH.sub.3 i-C.sub.3 H.sub.7                    
                                              O O Oil                     
109                                                                       
      ##STR224##            CH.sub.3 C.sub.2 H.sub.5                      
                                              O O 115-117                 
110                                                                       
      ##STR225##            C.sub.2 H.sub.5                               
                                     CH.sub.3 O O 129-130                 
111                                                                       
      ##STR226##                                                          
                             ##STR227##                                   
                                     C.sub.2 H.sub.5                      
                                              O O Oil                     
112  (CH.sub.3).sub.3 C     CH.sub.3 (CH.sub.2).sub.2 OC.sub.2 H.sub.5    
                                              O O  58                     
113  ClCH.sub.2 C(CH.sub.3).sub.2                                         
                            CH.sub.3 (CH.sub.2).sub.2 OC.sub.2 H.sub.5    
                                              O O Oil                     
114                                                                       
      ##STR228##            CH.sub.3 (CH.sub.2).sub.2 OC.sub.2 H.sub.5    
                                              O O 126-128                 
115                                                                       
      ##STR229##            CH.sub.3 (CH.sub.2).sub.2 OC.sub.2 H.sub.5    
                                              O O Oil                     
116                                                                       
      ##STR230##            CH.sub.3 (CH.sub.2).sub.2 OCH.sub.3           
                                              O O Oil                     
117                                                                       
      ##STR231##            CH.sub.3 (CH.sub.2).sub.2 OCH.sub.3           
                                              O O Oil                     
118                                                                       
      ##STR232##            CH.sub.3 CH.sub.3 O O  83                     
119                                                                       
      ##STR233##            CH.sub.3 CH.sub.3 O O 169                     
120                                                                       
      ##STR234##            CH.sub.3 CH.sub.3 O O 117                     
121  (CH.sub.3).sub.2 CHCH.sub.2                                          
                            CH.sub.3 CH.sub.3 O O 120                     
122                                                                       
      ##STR235##            CH.sub.3 CH.sub.3 O O 171                     
123  n-C.sub.3 H.sub.7 C(CH.sub.3).sub.2                                  
                            CH.sub.3 CH.sub.3 O O 147                     
124                                                                       
      ##STR236##            CH.sub.3 CH.sub.3 O O 139                     
125                                                                       
      ##STR237##            CH.sub.3 CH.sub.3 O O 165                     
126  CH.sub.3 C(C.sub.2 H.sub.5).sub.2                                    
                            CH.sub.3 CH.sub.3 O O 149                     
127                                                                       
      ##STR238##            CH.sub.3 CH.sub.3 O O  92                     
128                                                                       
      ##STR239##            CH.sub.3 CH.sub.3 O O 105                     
129                                                                       
      ##STR240##            CH.sub.3 CH.sub.3 O O 104                     
130                                                                       
      ##STR241##            CH.sub.3 CH.sub.3 O O 182                     
131                                                                       
      ##STR242##            CH.sub.3 CH.sub.3 O O  61                     
132  (C.sub.2 H.sub.5).sub.3 C                                            
                            CH.sub.3 CH.sub.3 O O 148                     
133  C.sub.2 H.sub.5 C(CH.sub.3).sub.2                                    
                            CH.sub.3 CH.sub.3 O O 151                     
134                                                                       
      ##STR243##            CH.sub.3 CH.sub.3 O O 126                     
135                                                                       
      ##STR244##            CH.sub.3 CH.sub.3 O O 128                     
136                                                                       
      ##STR245##            CH.sub.3 CH.sub.3 O O 146                     
137  n-C.sub.6 H.sub.13     CH.sub.3 CH.sub.3 O O 110                     
138  (CH.sub.3).sub.3 CCH.sub.2 C(CH.sub.3).sub.2                         
                            CH.sub.3 CH.sub.3 O O 150                     
139                                                                       
      ##STR246##            CH.sub.3 CH.sub.3 O O 126                     
140  HCCC(CH.sub.3).sub.2   CH.sub.3 CH.sub.3 O O 198                     
141                                                                       
      ##STR247##            CH.sub.3 CH.sub.3 O O 165                     
142                                                                       
      ##STR248##            CH.sub.3 CH.sub.3 O O 154                     
143  (CH.sub.3).sub.2 CHCH.sub.2 CH.sub.2                                 
                            CH.sub.3 CH.sub.3 O O 135                     
144  (CH.sub.3).sub.2 CHC(CH.sub.3).sub.2                                 
                            CH.sub.3 CH.sub.3 O O 158                     
145  Cl.sub.2 CHC(CH.sub.3).sub.2                                         
                            CH.sub.3 CH.sub.3 O O 153                     
146                                                                       
      ##STR249##            CH.sub.3 CH.sub.3 O O 129                     
147  n-C.sub.5 H.sub.11     CH.sub.3 CH.sub.3 O O 107                     
148  (C.sub.2 H.sub.5).sub.2 CHCH.sub.2                                   
                            CH.sub.3 CH.sub.3 O O  91                     
149                                                                       
      ##STR250##            CH.sub.3 CH.sub.3 O O  85                     
150  (CH.sub.3).sub.2 CH    CH.sub.3 CH.sub.3 O O 118                     
151  (ClCH.sub.2).sub.2 C(CH.sub.3)                                       
                            CH.sub.3 CH.sub.3 O O 153                     
152  FCH.sub.2 C(CH.sub.3).sub.2                                          
                            CH.sub.3 CH.sub.3 O O 151                     
153                                                                       
      ##STR251##            CH.sub.3 CH.sub.3 O O 123                     
154                                                                       
      ##STR252##            CH.sub.3 CH.sub.3 O O  91                     
155                                                                       
      ##STR253##            CH.sub.3 CH.sub.3 O O 173                     
156                                                                       
      ##STR254##            CH.sub.3 CH.sub.3 O O 149                     
157                                                                       
      ##STR255##            CH.sub.3 CH.sub.3 O O 147                     
158                                                                       
      ##STR256##            CH.sub.3 CH.sub.3 O O  87                     
159                                                                       
      ##STR257##            CH.sub.3 CH.sub.3 O O 162                     
160                                                                       
      ##STR258##            CH.sub.3 CH.sub.3 O O  60                     
161  n-C.sub.3 H.sub.7      CH.sub.3 CH.sub.3 O O 107                     
162                                                                       
      ##STR259##            CH.sub.3 CH.sub.3 O O 131                     
163  ClCH.sub.2 CH.sub.2    CH.sub.3 CH.sub.3 O O 117                     
164                                                                       
      ##STR260##            CH.sub.3 CH.sub.3 O O  96                     
165                                                                       
      ##STR261##            CH.sub.3 CH.sub.3 O O  86                     
166                                                                       
      ##STR262##            CH.sub.3 CH.sub.3 O O  85                     
167                                                                       
      ##STR263##            CH.sub.3 CH.sub.3 O O  90                     
168                                                                       
      ##STR264##            CH.sub.3 CH.sub.3 O O 107                     
169                                                                       
      ##STR265##            CH.sub.3 CH.sub.3 O O  94                     
170                                                                       
      ##STR266##            CH.sub.3 CH.sub.3 O O 122                     
171                                                                       
      ##STR267##            CH.sub.3 CH.sub.3 O O 137                     
172                                                                       
      ##STR268##            CH.sub.3 CH.sub.3 O O 139                     
173                                                                       
      ##STR269##            CH.sub.3 CH.sub.3 O O  91                     
174                                                                       
      ##STR270##            CH.sub.3 CH.sub.3 O O  59                     
__________________________________________________________________________
PREPARATION EXAMPLES OF COMPOUNDS OF FORMULA X Example 175 ##STR271## (Process (a))
A mixture of 2.0 g (10.5 mmol) of 4-methyl-5-phenoxy-2,4-dihydro-3H-1,2,4-triazol-3-one, 3.5 g (14.5 mmol) of 2-methoxycarbonyl-phenylsulphonyl isocyanate and 60 ml of acetonitrile is stirred for 6 hours at 20° C. and subsequently concentrated under a water pump vacuum. The residue is stirred with diethyl ether and the product which has precipitated in crystalline form is isolated by filtration with suction.
4.1 g (90% of theory) of 2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-phenoxy-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 161° C. are obtained.
Other examples of compounds of the formula (X) which can be prepared analogously to Example 175 and following the general description of the preparation processes according to the invention are those listed in Table 5 below. ##STR272##
                                  TABLE 5                                 
__________________________________________________________________________
Preparation Examples of the compounds of the                              
formula (X)                                                               
Example                                Melting                            
No.  R.sup.2   R.sup.3     R.sup.a     point (°C.)                 
__________________________________________________________________________
176                                                                       
               C.sub.2 H.sub.5                                            
                            ##STR273## 183                                
177  CH.sub.3                                                             
                ##STR274##                                                
                            ##STR275## 190                                
178  CH.sub.3  C.sub.3 H.sub.7                                            
                            ##STR276## 120                                
179  CH.sub.3  C.sub.3 H.sub.7                                            
                            ##STR277## 134                                
180  CH.sub.3  C.sub.3 H.sub.7                                            
                            ##STR278## 122                                
181  CH.sub.3  C.sub.3 H.sub.7                                            
                            ##STR279## 125                                
182  CH.sub.3  C.sub.2 H.sub.5                                            
                            ##STR280## 166-167                            
183  CH.sub.3  C.sub.2 H.sub.5                                            
                            ##STR281## 131-132                            
184  CH.sub.3  C.sub.2 H.sub.5                                            
                            ##STR282## 147-148                            
185  CH.sub.3  C.sub.2 H.sub.5                                            
                            ##STR283## 186-187                            
186  CH.sub.3  C.sub.2 H.sub.5                                            
                            ##STR284## 125-126                            
187  CH.sub.3  C.sub.2 H.sub.5                                            
                            ##STR285## 123-124                            
188  CH.sub.3  C.sub.2 H.sub.5                                            
                            ##STR286## 188-189                            
189  CH.sub.3  C.sub.2 H.sub.5                                            
                            ##STR287## 175-176                            
190  CH.sub.3  C.sub.2 H.sub.5                                            
                            ##STR288## 152-153                            
191  CH.sub.3  C.sub.2 H.sub.5                                            
                            ##STR289## 172-173                            
192  CH.sub.3  C.sub.2 H.sub.5                                            
                            ##STR290## 147-148                            
193  CH.sub.3  C.sub.2 H.sub.5                                            
                            ##STR291## 183-184                            
194  CH.sub.3  C.sub.2 H.sub.5                                            
                            ##STR292## 178-183                            
195  CH.sub.3  C.sub.2 H.sub.5                                            
                            ##STR293## 155-156                            
196  CH.sub.3  C.sub.2 H.sub.5                                            
                            ##STR294## 162-163                            
197  CH.sub.3  C.sub.2 H.sub.5                                            
                            ##STR295## 146-147                            
198  C.sub.3 H.sub.7                                                      
               CH.sub.3                                                   
                            ##STR296## 129-130                            
199  C.sub.3 H.sub.7                                                      
               CH.sub.3                                                   
                            ##STR297## 150-151                            
200  C.sub.3 H.sub.7                                                      
               CH.sub.3                                                   
                            ##STR298## 130-131                            
201  C.sub.3 H.sub.7                                                      
               CH.sub.3                                                   
                            ##STR299## 135-136                            
202  C.sub.3 H.sub.7                                                      
               CH.sub.3                                                   
                            ##STR300## 126-127                            
203  C.sub.3 H.sub.7                                                      
               CH.sub.3                                                   
                            ##STR301## 116-117                            
204  C.sub.3 H.sub.7                                                      
               CH.sub.3                                                   
                            ##STR302## 129-130                            
205  C.sub.3 H.sub.7                                                      
               CH.sub.3                                                   
                            ##STR303## 156-157                            
206  C.sub.3 H.sub.7                                                      
               CH.sub.3                                                   
                            ##STR304## 117-118                            
207  C.sub.3 H.sub.7                                                      
               CH.sub.3                                                   
                            ##STR305## 139-140                            
208  C.sub.3 H.sub.7                                                      
               CH.sub.3                                                   
                            ##STR306## 115-116                            
209  C.sub.3 H.sub.7                                                      
               CH.sub.3                                                   
                            ##STR307## 183-184                            
210  C.sub.3 H.sub.7                                                      
               CH.sub.3                                                   
                            ##STR308## 130-131                            
211  C.sub.3 H.sub.7                                                      
               CH.sub.3                                                   
                            ##STR309## 108-109                            
212  C.sub.3 H.sub.7                                                      
               CH.sub.3                                                   
                            ##STR310## 122-123                            
213  C.sub.3 H.sub.7                                                      
               CH.sub.3                                                   
                            ##STR311## 128-129                            
214  CH.sub.3  C.sub.4 H.sub.9                                            
                            ##STR312##  76                                
215  CH.sub.3  C.sub.4 H.sub.9                                            
                            ##STR313## 197                                
216  CH.sub.3  C.sub.4 H.sub.9                                            
                            ##STR314## 153                                
217  CH.sub.3  C.sub.4 H.sub.9                                            
                            ##STR315## 105                                
218  CH.sub.3  C.sub.4 H.sub.9                                            
                            ##STR316##  81                                
219  CH.sub.3  C.sub.4 H.sub.9                                            
                            ##STR317## 137                                
220  CH.sub.3  C.sub.4 H.sub.9                                            
                            ##STR318## 148                                
221  CH.sub.3  C.sub.4 H.sub.9                                            
                            ##STR319## 114                                
222  CH.sub.3  C.sub.4 H.sub.9                                            
                            ##STR320## 147                                
223  CH.sub.3  C.sub.4 H.sub.9                                            
                            ##STR321## 139                                
224                                                                       
      ##STR322##                                                          
               C.sub.2 H.sub.5                                            
                            ##STR323## 114                                
225                                                                       
      ##STR324##                                                          
               C.sub.2 H.sub.5                                            
                            ##STR325## 135                                
226                                                                       
      ##STR326##                                                          
               C.sub.2 H.sub.5                                            
                            ##STR327## 108                                
227  CH.sub.3                                                             
                ##STR328##                                                
                            ##STR329## 209                                
228  CH.sub.3                                                             
                ##STR330##                                                
                            ##STR331## 191                                
229  CH.sub.3                                                             
                ##STR332##                                                
                            ##STR333## 207                                
230  CH.sub.3  CH.sub.3                                                   
                            ##STR334## 154                                
231  CH.sub.3  CH.sub.3                                                   
                            ##STR335## 187                                
232  CH.sub.3  CH.sub.3                                                   
                            ##STR336## 179                                
233  CH.sub.2 CHCH.sub.2                                                  
               CH.sub.3                                                   
                            ##STR337## 124                                
234  CH.sub.2 CHCH.sub.2                                                  
               CH.sub.3                                                   
                            ##STR338## 153                                
235  CH.sub.2 CHCH.sub.2                                                  
               CH.sub.3                                                   
                            ##STR339## 150                                
236  CH.sub.2 CHCH.sub.2                                                  
               CH.sub.3                                                   
                            ##STR340## 103                                
237  CH.sub.2 CHCH.sub.2                                                  
               CH.sub.3                                                   
                            ##STR341## 130                                
238  CH.sub.3  CH.sub.3                                                   
                            ##STR342## 196                                
239  CH.sub.3  CH.sub.3                                                   
                            ##STR343## 136                                
240  CH.sub.2 CHCH.sub.2                                                  
               CH.sub.3                                                   
                            ##STR344## 130                                
241  CH.sub.3                                                             
                ##STR345##                                                
                            ##STR346## 211                                
242  CH.sub.3                                                             
                ##STR347##                                                
                            ##STR348## 179                                
243  CH.sub.3  CH.sub.3                                                   
                            ##STR349## 171                                
244  CH.sub.2 CHCH.sub.2                                                  
               CH.sub.3                                                   
                            ##STR350## 115                                
245  CH.sub.3                                                             
                ##STR351##                                                
                            ##STR352## 162                                
246  CH.sub.3  C.sub.3 H.sub.7                                            
                            ##STR353## 141                                
247  CH.sub.3  CH.sub.3                                                   
                            ##STR354## 148                                
248  CH.sub.3                                                             
                ##STR355##                                                
                            ##STR356## 174                                
249  CH.sub.2 CHCH.sub.2                                                  
               CH.sub.3                                                   
                            ##STR357## 138                                
250                                                                       
      ##STR358##                                                          
               CH.sub.3                                                   
                            ##STR359## 148                                
251                                                                       
      ##STR360##                                                          
               CH.sub.3                                                   
                            ##STR361## 150                                
252  CH.sub.2 CHCH.sub.2                                                  
               CH.sub.3                                                   
                            ##STR362## 125                                
253  CH.sub.3  CH.sub.3                                                   
                            ##STR363## 145                                
254  C.sub.2 H.sub.5                                                      
               CH.sub.3                                                   
                            ##STR364## 153-154                            
255  C.sub.2 H.sub.5                                                      
               CH.sub.3                                                   
                            ##STR365## 151-152                            
256  C.sub.2 H.sub.5                                                      
               CH.sub.3                                                   
                            ##STR366## 167-168                            
257  C.sub.2 H.sub.5                                                      
               CH.sub.3                                                   
                            ##STR367## 155-156                            
258  C.sub.2 H.sub.5                                                      
               CH.sub.3                                                   
                            ##STR368## 174-175                            
259  C.sub.2 H.sub.5                                                      
               CH.sub.3                                                   
                            ##STR369## 140-141                            
260  C.sub.2 H.sub.5                                                      
               CH.sub.3                                                   
                            ##STR370## 160                                
261  C.sub.2 H.sub.5                                                      
               CH.sub.3                                                   
                            ##STR371## 146-147                            
262  C.sub.2 H.sub.5                                                      
               CH.sub.3                                                   
                            ##STR372## 156-157                            
263  C.sub.2 H.sub.5                                                      
               CH.sub.3                                                   
                            ##STR373## 125-126                            
264  C.sub.2 H.sub.5                                                      
               CH.sub.3                                                   
                            ##STR374## 137-138                            
265  C.sub.2 H.sub.5                                                      
               CH.sub.3                                                   
                            ##STR375## 203-204                            
266  CH.sub.3  C.sub.4 H.sub.9                                            
                            ##STR376## 118-119                            
267  CH.sub.3  C.sub.4 H.sub.9                                            
                            ##STR377## 146-147                            
268  CH.sub.3  C.sub.4 H.sub.9                                            
                            ##STR378## 110-111                            
269  CH.sub.3  C.sub.4 H.sub.9                                            
                            ##STR379## 123-124                            
270                                                                       
      ##STR380##                                                          
               C.sub.2 H.sub.5                                            
                            ##STR381## 152-153                            
271                                                                       
      ##STR382##                                                          
               C.sub.2 H.sub.5                                            
                            ##STR383## 116-117                            
272                                                                       
      ##STR384##                                                          
               C.sub.2 H.sub.5                                            
                            ##STR385## 145-146                            
273                                                                       
      ##STR386##                                                          
               C.sub.2 H.sub.5                                            
                            ##STR387## 132-133                            
274                                                                       
      ##STR388##                                                          
               C.sub.2 H.sub.5                                            
                            ##STR389## 88-89                              
275                                                                       
      ##STR390##                                                          
               C.sub.2 H.sub.5                                            
                            ##STR391## 128-129                            
276                                                                       
      ##STR392##                                                          
               C.sub.2 H.sub.5                                            
                            ##STR393## 79-77                              
277  CH.sub.2 CHCH.sub.2                                                  
               C.sub.2 H.sub.5                                            
                            ##STR394## 114-115                            
278  CH.sub.2 CHCH.sub.2                                                  
               C.sub.2 H.sub.5                                            
                            ##STR395## 104-106                            
279  CH.sub.2 CHCH.sub.2                                                  
               C.sub.2 H.sub.5                                            
                            ##STR396## 85-86                              
280  CH.sub.2 CHCH.sub.2                                                  
               C.sub.2 H.sub.5                                            
                            ##STR397## 121-122                            
281  CH.sub.2 CHCH.sub.2                                                  
               C.sub.2 H.sub.5                                            
                            ##STR398## 107-108                            
282  CH.sub.2 CHCH.sub.2                                                  
               C.sub.2 H.sub.5                                            
                            ##STR399## 123-124                            
283  CH.sub.2 CHCH.sub.2                                                  
               C.sub.2 H.sub.5                                            
                            ##STR400## 131-132                            
284  CH.sub.2 CHCH.sub.2                                                  
               C.sub.2 H.sub.5                                            
                            ##STR401## 118-119                            
285  CH.sub.2 CHCH.sub.2                                                  
               C.sub.2 H.sub.5                                            
                            ##STR402## 110-111                            
286  CH.sub.2 CHCH.sub.2                                                  
               C.sub.2 H.sub.5                                            
                            ##STR403## 123-124                            
287  CH.sub.2 CHCH.sub.2                                                  
               C.sub.2 H.sub.5                                            
                            ##STR404## 103-104                            
288  CH.sub.2 CHCH.sub.2                                                  
               C.sub.2 H.sub.5                                            
                            ##STR405## >250                               
289  CH.sub.2 CHCH.sub.2                                                  
               C.sub.2 H.sub.5                                            
                            ##STR406## 114-115                            
290  CH.sub.2 CHCH.sub.2                                                  
               C.sub.2 H.sub.5                                            
                            ##STR407## 122-123                            
291  CH(CH.sub.3).sub.2                                                   
               C.sub.2 H.sub.5                                            
                            ##STR408## 188-190                            
292  CH(CH.sub.3).sub.2                                                   
               C.sub.2 H.sub.5                                            
                            ##STR409## 230-231                            
293  CH(CH.sub.3).sub.2                                                   
               C.sub.2 H.sub.5                                            
                            ##STR410## 129-130                            
294  CH(CH.sub.3).sub.2                                                   
               C.sub.2 H.sub.5                                            
                            ##STR411## 207 (Zers.)                        
295  CH(CH.sub.3).sub.2                                                   
               C.sub.2 H.sub.5                                            
                            ##STR412## 113-114                            
296  CH(CH.sub.3).sub.2                                                   
               C.sub.2 H.sub.5                                            
                            ##STR413## 195-200                            
297  CH(CH.sub.3).sub.2                                                   
               C.sub.2 H.sub.5                                            
                            ##STR414## 133-134                            
298  CH(CH.sub.3).sub.2                                                   
               C.sub.2 H.sub.5                                            
                            ##STR415## 139-140                            
299  CH(CH.sub.3).sub.2                                                   
               C.sub.2 H.sub.5                                            
                            ##STR416## 105-106                            
300  CH(CH.sub.3).sub.2                                                   
               C.sub.2 H.sub.5                                            
                            ##STR417## 123-124                            
301  (CH.sub.2).sub.3 OCH.sub.3                                           
               CH.sub.3                                                   
                            ##STR418## 112-114                            
302  (CH.sub.2).sub.3 OCH.sub.3                                           
               CH.sub.3                                                   
                            ##STR419## 92-95                              
303  (CH.sub.2).sub.3 OCH.sub.3                                           
               CH.sub.3                                                   
                            ##STR420## 126-127                            
304  (CH.sub.2).sub.3 OCH.sub.3                                           
               CH.sub.3                                                   
                            ##STR421## 115-116                            
305  (CH.sub.2).sub.3 OCH.sub.3                                           
               CH.sub.3                                                   
                            ##STR422## 112-113                            
306  (CH.sub.2).sub.3 OCH.sub.3                                           
               CH.sub.3                                                   
                            ##STR423## 81-82                              
307  (CH.sub.2).sub.3 OCH.sub.3                                           
               CH.sub.3                                                   
                            ##STR424## 104-105                            
308  (CH.sub.2).sub.3 OCH.sub.3                                           
               CH.sub.3                                                   
                            ##STR425## 113-114                            
309  (CH.sub.2).sub.3 OCH.sub.3                                           
               CH.sub.3                                                   
                            ##STR426## 91-92                              
310  n-C.sub.3 H.sub.7                                                    
               C.sub.2 H.sub.5                                            
                            ##STR427## 108 (Zers.)                        
311  n-C.sub.3 H.sub.7                                                    
               C.sub.2 H.sub.5                                            
                            ##STR428## 212-213                            
312  n-C.sub.3 H.sub.7                                                    
               C.sub.2 H.sub.5                                            
                            ##STR429## 106-107                            
313  n-C.sub.3 H.sub.7                                                    
               C.sub.2 H.sub.5                                            
                            ##STR430## 127-128                            
314  n-C.sub.3 H.sub.7                                                    
               C.sub.2 H.sub.5                                            
                            ##STR431##  95 (Zers.)                        
315  n-C.sub.3 H.sub.7                                                    
               C.sub.2 H.sub.5                                            
                            ##STR432## 132-135                            
316  n-C.sub.3 H.sub.7                                                    
               C.sub.2 H.sub.5                                            
                            ##STR433## 138-140                            
317  n-C.sub.3 H.sub.7                                                    
               C.sub.2 H.sub.5                                            
                            ##STR434## 87-88                              
318  n-C.sub.3 H.sub.7                                                    
               C.sub.2 H.sub.5                                            
                            ##STR435## 108-109                            
319  n-C.sub.3 H.sub.7                                                    
               C.sub.2 H.sub.5                                            
                            ##STR436## 154-157                            
320  n-C.sub.3 H.sub.7                                                    
               C.sub.2 H.sub.5                                            
                            ##STR437## 130-133                            
321  CH(CH.sub.3).sub.2                                                   
               CH.sub.3                                                   
                            ##STR438## 150-151                            
322  CH(CH.sub.3).sub.2                                                   
               CH.sub.3                                                   
                            ##STR439## 160-161                            
323  CH(CH.sub.3).sub.2                                                   
               CH.sub.3                                                   
                            ##STR440## 147-148                            
324  CH(CH.sub.3).sub.2                                                   
               CH.sub.3                                                   
                            ##STR441## 148-150                            
324  CH(CH.sub.3).sub.2                                                   
               CH.sub.3                                                   
                            ##STR442## 143-144                            
326  CH(CH.sub.3).sub.2                                                   
               CH.sub.3                                                   
                            ##STR443## 134-135                            
327  CH(CH.sub.3).sub.2                                                   
               CH.sub.3                                                   
                            ##STR444## 147-150                            
328  CH(CH.sub.3).sub.2                                                   
               CH.sub.3                                                   
                            ##STR445## 148-150                            
329  CH(CH.sub.3).sub.2                                                   
               CH.sub.3                                                   
                            ##STR446## 143-145                            
330  CH(CH.sub.3).sub.2                                                   
               CH.sub.3                                                   
                            ##STR447## 114-116                            
331  CH(CH.sub.3).sub.2                                                   
               CH.sub.3                                                   
                            ##STR448## 125-128                            
332  CH.sub.3  CH(CH.sub.3).sub.2                                         
                            ##STR449## 95-97                              
333  CH.sub.3  CH(CH.sub.3).sub.2                                         
                            ##STR450## 158-160                            
334  CH.sub.3  CH(CH.sub.3).sub.2                                         
                            ##STR451## 152-153                            
335  CH.sub.3  CH(CH.sub.3).sub.2                                         
                            ##STR452## 150-152                            
336  CH.sub.3  CH(CH.sub.3).sub.2                                         
                            ##STR453## 128-130                            
337  CH.sub.3  CH(CH.sub.3).sub.2                                         
                            ##STR454## 150-152                            
338  CH.sub.3                                                             
                ##STR455##                                                
                            ##STR456## 117-118                            
339  CH.sub.3                                                             
                ##STR457##                                                
                            ##STR458## 130-132                            
340                                                                       
      ##STR459##                                                          
               C.sub.2 H.sub.5                                            
                            ##STR460## 148-150                            
341  C.sub.2 H.sub.5                                                      
               CH.sub.3                                                   
                            ##STR461## 172-173                            
342  CH.sub.2 CHCH.sub.2                                                  
               C.sub.2 H.sub.5                                            
                            ##STR462## 130-132                            
343  CH(CH.sub.3).sub.2                                                   
               C.sub.2 H.sub.5                                            
                            ##STR463## 142-144                            
344  (CH.sub.2).sub.3 OCH.sub.3                                           
               CH.sub.3                                                   
                            ##STR464## 127-130                            
345  n-C.sub.3 H.sub.7                                                    
               C.sub.2 H.sub.5                                            
                            ##STR465## 127-130                            
346  CH(CH.sub.3).sub.2                                                   
               CH.sub.3                                                   
                            ##STR466## 156-157                            
347  CH.sub.3  CH(CH.sub.3).sub.2                                         
                            ##STR467## 198-200                            
348  CH(CH.sub.3).sub.2                                                   
               C.sub.2 H.sub.5                                            
                            ##STR468## 122-124                            
349  (CH.sub.2).sub.3 OCH.sub.3                                           
               CH.sub.3                                                   
                            ##STR469## 97-98                              
350  n-C.sub.3 H.sub.7                                                    
               C.sub.2 H.sub.5                                            
                            ##STR470## 128-130                            
351  CH(CH.sub.3).sub.2                                                   
               CH.sub.3                                                   
                            ##STR471## 148-150                            
352  CH.sub.3  CH(CH.sub.3).sub.2                                         
                            ##STR472## 154                                
353  C.sub.2 H.sub.5                                                      
               CH.sub.3                                                   
                            ##STR473## 145                                
354  CH.sub.3  C.sub.2 H.sub.5                                            
                            ##STR474## 134-136                            
355  CH.sub.3  C.sub.2 H.sub.5                                            
                            ##STR475## 178                                
356  CH.sub.3  n-C.sub.4 H.sub.9                                          
                            ##STR476## 142-143                            
357  C.sub.2 H.sub.5                                                      
               CH.sub.3                                                   
                            ##STR477## 115-118                            
358  CH.sub.2 CHCH.sub.2                                                  
               C.sub.2 H.sub.5                                            
                            ##STR478## 98-99                              
359  CH.sub.3  C.sub.2 H.sub.5                                            
                            ##STR479## 114-115 (Na-Salz)                  
360  CH.sub.3  C.sub.2 H.sub.5                                            
                            ##STR480## 135-140 (Na-Salz)                  
361  CH.sub.3  CH.sub.3                                                   
                            ##STR481## 161-163 (Na-Salz)                  
362  CH.sub.3  C.sub.6 H.sub.5                                            
                            ##STR482## 185                                
363  CH.sub.3  C.sub.6 H.sub.5                                            
                            ##STR483## 202                                
364  CH.sub.3  C.sub.2 H.sub.5                                            
                            ##STR484## 160 (sodium salt)                  
365  CH.sub.3  C.sub.2 H.sub.5                                            
                            ##STR485## 144 (sodium salt)                  
366  C.sub.2 H.sub.5                                                      
               CH.sub.3                                                   
                            ##STR486## 180 (sodium salt)                  
367  CH.sub.3  n-C.sub.4 H.sub.9                                          
                            ##STR487## >270  (sodium salt)                
368  CH.sub.3  C.sub.2 H.sub.5                                            
                            ##STR488## 124 (sodium salt)                  
369  CH.sub.3  i-C.sub.3 H.sub.7                                          
                            ##STR489## 160                                
370  CH.sub.3  i-C.sub.3 H.sub.7                                          
                            ##STR490## 167                                
371  CH.sub.3  i-C.sub.3 H.sub.7                                          
                            ##STR491## 166                                
372  CH.sub.3  i-C.sub.3 H.sub.7                                          
                            ##STR492## 145                                
373  CH.sub.3  i-C.sub.3 H.sub.7                                          
                            ##STR493## 126                                
374  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                           
                            ##STR494## 113                                
375  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                           
                            ##STR495## 102                                
376  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                           
                            ##STR496## 103                                
377  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                           
                            ##STR497## 114                                
378  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                           
                            ##STR498## 105                                
379  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                           
                            ##STR499## 135                                
380  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                           
                            ##STR500## 147                                
381  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                           
                            ##STR501## 127                                
382  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                           
                            ##STR502## 130                                
383  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                           
                            ##STR503## 137                                
384  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                           
                            ##STR504## 127                                
385  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                           
                            ##STR505## 155                                
386  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                           
                            ##STR506## 150                                
387  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                  
                            ##STR507## 120                                
388  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                  
                            ##STR508## 109                                
389  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                  
                            ##STR509## 146                                
390  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                  
                            ##STR510## 150                                
391  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                  
                            ##STR511## 170                                
392  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                  
                            ##STR512## 148                                
393  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                  
                            ##STR513## 130                                
394  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                  
                            ##STR514## 110                                
395  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                  
                            ##STR515## 164                                
396  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                  
                            ##STR516## 122                                
397  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                  
                            ##STR517##  92                                
398  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                  
                            ##STR518##  98                                
399  C.sub.2 H.sub.5                                                      
               C.sub.2 H.sub.4 OCH.sub.3                                  
                            ##STR519##  76                                
400  C.sub.2 H.sub.5                                                      
               C.sub.2 H.sub.4 OCH.sub.3                                  
                            ##STR520##  88                                
401  C.sub.2 H.sub.5                                                      
               C.sub.2 H.sub.4 OCH.sub.3                                  
                            ##STR521##  84                                
402  C.sub.2 H.sub.5                                                      
               C.sub.2 H.sub.4 OCH.sub.3                                  
                            ##STR522##  80                                
403  C.sub.2 H.sub.5                                                      
               C.sub.2 H.sub.4 OCH.sub.3                                  
                            ##STR523##  76                                
404  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                           
                            ##STR524## 123                                
405  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                           
                            ##STR525## 122                                
406  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                  
                            ##STR526## 129                                
407  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                  
                            ##STR527## 132                                
408  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                  
                            ##STR528## 122                                
409  C.sub.2 H.sub.5                                                      
               C.sub.2 H.sub.4 OCH.sub.3                                  
                            ##STR529##  87                                
410  C.sub.2 H.sub.5                                                      
               C.sub.2 H.sub.4 OCH.sub.3                                  
                            ##STR530##  78                                
411  C.sub.2 H.sub.5                                                      
               C.sub.2 H.sub.4 OCH.sub.3                                  
                            ##STR531## 106                                
412  C.sub.2 H.sub.5                                                      
               C.sub.2 H.sub.4 OCH.sub.3                                  
                            ##STR532##  75                                
413  C.sub.2 H.sub.5                                                      
               C.sub.2 H.sub.4 OCH.sub.3                                  
                            ##STR533##  80                                
414  C.sub.2 H.sub.5                                                      
               C.sub.2 H.sub.4 OCH.sub.3                                  
                            ##STR534##  78                                
415  C.sub.2 H.sub.5                                                      
               C.sub.2 H.sub.4 OCH.sub.3                                  
                            ##STR535##  74                                
416  C.sub.2 H.sub.5                                                      
               C.sub.2 H.sub.4 OCH.sub.3                                  
                            ##STR536##  78                                
417  C.sub.2 H.sub.5                                                      
               C.sub.2 H.sub.4 OCH.sub.3                                  
                            ##STR537##  68                                
418  C.sub.2 H.sub.5                                                      
               C.sub.2 H.sub.4 OCH.sub.3                                  
                            ##STR538##  98                                
419  CH.sub.3  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 -i                        
                            ##STR539##  88                                
420  CH.sub.3  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 -i                        
                            ##STR540##  98                                
421  CH.sub.3  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 -i                        
                            ##STR541## 106                                
422  CH.sub.3  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 -i                        
                            ##STR542## 106                                
423  CH.sub.3  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 -i                        
                            ##STR543##  92                                
424  CH.sub.3  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 -i                        
                            ##STR544## 136                                
425  CH.sub.3  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 -i                        
                            ##STR545## 123                                
426  CH.sub.3  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 -i                        
                            ##STR546## 122                                
427  CH.sub.3  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 -i                        
                            ##STR547## 116                                
428  CH.sub.3                                                             
                ##STR548##                                                
                            ##STR549##  78                                
429  CH.sub.3  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 -i                        
                            ##STR550## 126                                
430  CH.sub.3                                                             
                ##STR551##                                                
                            ##STR552## 114                                
431  CH.sub.3                                                             
                ##STR553##                                                
                            ##STR554## 106                                
432  CH.sub.3                                                             
                ##STR555##                                                
                            ##STR556## 107                                
433  CH.sub.3  i-C.sub.3 H.sub.7                                          
                            ##STR557## 145                                
434  CH.sub.3  C.sub.2 H.sub.5                                            
                            ##STR558## 140 (sodium salt)                  
435  CH.sub.3  C.sub.2 H.sub.5                                            
                            ##STR559## 140 (sodium salt)                  
436  CH.sub.3                                                             
                ##STR560##                                                
                            ##STR561## 100                                
437  CH.sub.3                                                             
                ##STR562##                                                
                            ##STR563##  99                                
438  CH.sub.3                                                             
                ##STR564##                                                
                            ##STR565##  86                                
439  CH.sub.3                                                             
                ##STR566##                                                
                            ##STR567## 119                                
440  CH.sub.3                                                             
                ##STR568##                                                
                            ##STR569## 119                                
441  CH.sub.3                                                             
                ##STR570##                                                
                            ##STR571##  93                                
442  CH.sub.3                                                             
                ##STR572##                                                
                            ##STR573## 111                                
443  CH.sub.3                                                             
                ##STR574##                                                
                            ##STR575## 113                                
444  CH.sub.3                                                             
                ##STR576##                                                
                            ##STR577##  86                                
445  CH.sub.3                                                             
                ##STR578##                                                
                            ##STR579## 175                                
446  CH.sub.3                                                             
                ##STR580##                                                
                            ##STR581##  90                                
447  CH.sub.3                                                             
                ##STR582##                                                
                            ##STR583##  95                                
448  CH.sub.3                                                             
                ##STR584##                                                
                            ##STR585##  95                                
449  CH.sub.3                                                             
                ##STR586##                                                
                            ##STR587## 130                                
450  CH.sub.3                                                             
                ##STR588##                                                
                            ##STR589##  77                                
451  CH.sub.3                                                             
                ##STR590##                                                
                            ##STR591##  80                                
452  CH.sub.3                                                             
                ##STR592##                                                
                            ##STR593##  92                                
453  CH.sub.3                                                             
                ##STR594##                                                
                            ##STR595##  74                                
454  CH.sub.3                                                             
                ##STR596##                                                
                            ##STR597## 108                                
455  CH.sub.3                                                             
                ##STR598##                                                
                            ##STR599## 112                                
456  CH.sub.3                                                             
                ##STR600##                                                
                            ##STR601## 103                                
457  CH.sub.3  CH.sub.3                                                   
                            ##STR602## 127                                
458  CH.sub.3  n-C.sub.3 H.sub.7                                          
                            ##STR603## 123                                
459                                                                       
      ##STR604##                                                          
               n-C.sub.3 H.sub.7                                          
                            ##STR605## 128                                
460  CH.sub.3  CH.sub.3                                                   
                            ##STR606## 179                                
461  CH.sub.3  CH.sub.3                                                   
                            ##STR607## 176                                
462  CH.sub.3  CH.sub.3                                                   
                            ##STR608## 178                                
463  CH.sub.3  CH.sub.3                                                   
                            ##STR609## 177                                
464                                                                       
      ##STR610##                                                          
               n-C.sub.3 H.sub.7                                          
                            ##STR611##  94                                
465                                                                       
      ##STR612##                                                          
               n-C.sub.3 H.sub.7                                          
                            ##STR613## 115                                
466                                                                       
      ##STR614##                                                          
               n-C.sub.3 H.sub.7                                          
                            ##STR615## 115                                
467                                                                       
      ##STR616##                                                          
               n-C.sub.3 H.sub.7                                          
                            ##STR617## 119                                
468  CH.sub.3  CH.sub.3                                                   
                            ##STR618## 170 (sodium salt)                  
469  CH.sub.3  CH.sub.3                                                   
                            ##STR619## 166                                
470  CH.sub.3  n-C.sub.3 H.sub.7                                          
                            ##STR620## 124                                
471  CH.sub.3  n-C.sub.3 H.sub.7                                          
                            ##STR621## 178 (sodium salt)                  
472  CH.sub.3  CH.sub.3                                                   
                            ##STR622## 192                                
473  CH.sub.3  CH.sub.3                                                   
                            ##STR623## 160                                
474  CH.sub.3  n-C.sub.3 H.sub.7                                          
                            ##STR624## 149                                
475  CH.sub.3  n-C.sub.3 H.sub.7                                          
                            ##STR625## 131                                
476  CH.sub.3  n-C.sub.3 H.sub.7                                          
                            ##STR626## 156                                
477  CH.sub.3  n-C.sub.3 H.sub.7                                          
                            ##STR627## 131                                
478  CH.sub.3  n-C.sub.3 H.sub.7                                          
                            ##STR628## 150                                
479  CH.sub.3  n-C.sub.3 H.sub.7                                          
                            ##STR629## 171                                
480  CH.sub.3  n-C.sub.3 H.sub.7                                          
                            ##STR630## 147                                
481  CH.sub.3  n-C.sub.3 H.sub.7                                          
                            ##STR631## 111                                
482  CH.sub.3  n-C.sub.3 H.sub.7                                          
                            ##STR632## 124                                
483  CH.sub.3  n-C.sub.3 H.sub.7                                          
                            ##STR633## 112                                
484                                                                       
      ##STR634##                                                          
               n-C.sub.3 H.sub.7                                          
                            ##STR635## 118                                
485                                                                       
      ##STR636##                                                          
               n-C.sub.3 H.sub.7                                          
                            ##STR637## 116                                
486                                                                       
      ##STR638##                                                          
               n-C.sub.3 H.sub.7                                          
                            ##STR639## 103                                
487                                                                       
      ##STR640##                                                          
               n-C.sub.3 H.sub.7                                          
                            ##STR641##  81                                
488                                                                       
      ##STR642##                                                          
               n-C.sub.3 H.sub.7                                          
                            ##STR643## 114                                
489                                                                       
      ##STR644##                                                          
               n-C.sub.3 H.sub.7                                          
                            ##STR645## 120                                
490                                                                       
      ##STR646##                                                          
               n-C.sub.3 H.sub.7                                          
                            ##STR647## 107                                
491                                                                       
      ##STR648##                                                          
               n-C.sub.3 H.sub.7                                          
                            ##STR649## 143                                
492                                                                       
      ##STR650##                                                          
               n-C.sub.3 H.sub.7                                          
                            ##STR651## 132                                
493  CH.sub.3  CH.sub.3                                                   
                            ##STR652## 121 (sodium salt)                  
494  CH.sub.3  n-C.sub.3 H.sub.7                                          
                            ##STR653## 188 (sodium salt)                  
495  CH.sub.3  CH.sub.3                                                   
                            ##STR654## 175 (sodium salt)                  
496                                                                       
      ##STR655##                                                          
               n-C.sub.3 H.sub.7                                          
                            ##STR656## 111                                
497  CH.sub.3                                                             
                ##STR657##                                                
                            ##STR658## 108                                
498  CH.sub.3  i-C.sub.4 H.sub.9                                          
                            ##STR659## 129                                
499  CH.sub.3                                                             
                ##STR660##                                                
                            ##STR661## 117                                
500  CH.sub.3  i-C.sub.4 H.sub.9                                          
                            ##STR662##  96                                
501  CH.sub.3  CH.sub.2 CF.sub.3                                          
                            ##STR663##                                    
__________________________________________________________________________
STARTING SUBSTANCES OF THE FORMULA (II) Example (II-1) ##STR664##
A mixture of 5.0 g (0.02 mol) of 1-phenoxycarbonyl-4-allyl-O-methyl-isosemicarbazide and 30 ml of toluene is refluxed for 15 minutes and subsequently concentrated under a water pump vacuum. The residue is triturated with diethyl ether/petroleum ether, and the product which has been obtained in crystalline form is isolated by filtration with suction.
2.0 g (64% of theory) of 4-allyl-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 111° C. are obtained.
Example (II-2) ##STR665##
50.2 g (0.33 mol) of phenyl hydrazinoformate and 36.6 g (0.33 mol, 93% strength) of trimethyl iminocarabonate are heated to 60° C. in 100 ml of absolute o-dichlorobenzene, and the mixture is stirred for 2 hours, during which process a clear mixture is stirred for 2 hours, during which process a clear solution is formed. In the course of two hours, it is heated to 120° C., during which process methanol distilled off. A vacuum is applied carefully, during which process more methanol and finally phenol distil off. Further distillation results in a fraction which solidifies in the receiving vessel in crystalline form.
After recrystallisation from toluene, 7.0 g (0.054 mol, 16% of theory) of 4-methyl-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 142°-144° C. are obtained in the form of colourless crystals. This compound in known from F. Arndt et al, Rev. faculte. Sci. Univ. Istanbul, 13A, 127 (1948).
Other examples of compounds of the formula (II) which can be prepared analogously to Examples (II-1) and (II-2) are those listed in Table 6 below. ##STR666##
                                  TABLE 6                                 
__________________________________________________________________________
Examples of the starting substances of the                                
formula (II)                                                              
Example                    Melting                                        
No.   R.sup.2  R.sup.3     point (°C.)                             
__________________________________________________________________________
II-3  CH.sub.3                                                            
                           163                                            
II-4  CH.sub.3 C.sub.3 H.sub.7                                            
                           72                                             
II-5                                                                      
       ##STR667##                                                         
               CH.sub.3    149                                            
II-6                                                                      
       ##STR668##                                                         
               C.sub.2 H.sub.5                                            
                           130                                            
II-7  CH(CH.sub.3).sub.2                                                  
               CH.sub.3    80-81                                          
II-8  C.sub.2 H.sub.5                                                     
               CH.sub.3    (b.p.: 120° C.                          
                           at 1.5 mbar)                                   
II-9  C.sub.3 H.sub.7                                                     
               CH.sub.3    (b.p.: 130-150° C.                      
                           at 1.5 mbar)                                   
II-10 CH.sub.3 C.sub.4 H.sub.9                                            
                           152-153                                        
II-11 (CH.sub.2).sub.3 OCH.sub.3                                          
               CH.sub.3    84-85                                          
II-12 CH.sub.3 C.sub.2 H.sub.5                                            
                           (b.p.: 140-150° C.                      
                           at 1.5 mbar)                                   
II-13 CH(CH.sub.3).sub.2                                                  
               C.sub.2 H.sub.5                                            
                           66-67                                          
II-14 C.sub.3 H.sub.7                                                     
               C.sub.2 H.sub.5                                            
                           (b.p.: 140-150° C.                      
                           at 1.5 mbar)                                   
II-15 CH.sub.2CHCH.sub.2                                                  
               C.sub.2 H.sub.5                                            
                           (b.p.: 150° C.                          
                           at 1.5 mbar)                                   
II-16                                                                     
       ##STR669##                                                         
               n-C.sub.3 H.sub.7                                          
                           100                                            
II-17 CH.sub.3                                                            
                ##STR670## 106                                            
II-18 CH.sub.3 i-C.sub.3 H.sub.7                                          
                           134                                            
II-19 CH.sub.3 C.sub.2 H.sub.4 OC.sub.2 H.sub.5                           
                           90                                             
II-20 CH.sub.3 C.sub.2 H.sub.4 OCH.sub.3                                  
                           125                                            
II-21 C.sub.2 H.sub.5                                                     
               C.sub.2 H.sub.4 OCH.sub.3                                  
                           94                                             
II-22 C.sub.2 H.sub.5                                                     
               C.sub.2 H.sub.4 OC.sub.3 H.sub.7 -i                        
                           92                                             
II-23 CH.sub.3                                                            
                ##STR671## 73                                             
II-24 CH.sub.3                                                            
                ##STR672## (Oil)                                          
II-25 CH.sub.3                                                            
                ##STR673## (Oil)                                          
II-26 CH.sub.3                                                            
                ##STR674## 37                                             
II-27 CH.sub.3 CH.sub.2 CH(CH.sub.3).sub.2                                
                           (amorphous)                                    
II-28 CH.sub.3 CH.sub.2 CHCH.sub.2                                        
                           69                                             
II-29 CH.sub.3 CH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                       
                           82                                             
II-30 CH.sub.3                                                            
                ##STR675## 116                                            
II-31 CH.sub.3 CH.sub.2 C(CH.sub.3).sub.3                                 
                           130                                            
__________________________________________________________________________
INTERMEDIATES OF THE FORMULA (XVII) Example (XVII-1) ##STR676##
A mixture of 30.4 g (0.2 mol) of phenyl hydrazinoformate, 26.0 g (0.2 mol) of methyl N-allyl-iminocarbonate and 150 ml of methanol is stirred for 12 hours at 20° C. and subsequently concentrated under a water pump vacuum. The residue is triturated with diethyl ether/ethanol (1/1 by vol.), and the crystalline product is isolated by filtration with suction.
11.0 g (22% of theory) of 1-phenoxycarbonyl-4-allyl-O-methyl-isosemicarbazide of melting point 114° C. are obtained.
Other examples of compounds of the formula (IX) which can be prepared analogously to Example (IX-1) are those listed in Table 5 below. ##STR677##
              TABLE 7                                                     
______________________________________                                    
Examples of the compounds of the formula (XVII)                           
Example                            Melting                                
No.       R.sup.2                                                         
                 R.sup.3  R.sup.4  point (°C.)                     
______________________________________                                    
XVII-2    CH.sub.3                                                        
                 CH.sub.3                                                 
                                   123                                    
XVII-3    C.sub.2 H.sub.5                                                 
                 CH.sub.3 C.sub.2 H.sub.5                                 
                                   137                                    
XVII-4    CH.sub.3                                                        
                 CH.sub.3 CH.sub.3 134                                    
XVII-5    CH.sub.3                                                        
                 CH.sub.3 C.sub.2 H.sub.5                                 
                                   135                                    
XVII-6    C.sub.2 H.sub.5                                                 
                 CH.sub.3                                                 
                           ##STR678##                                     
                                   133-134                                
______________________________________
USE EXAMPLES
In the Use Examples, the following compound (A) is used as comparison substance: ##STR679##
4-amino-5-methyl-2-phenylaminocarbonyl-2,4-dihydro-3-H-1,2,4-triazol-3-one (disclosed in EP-A 294,666).
Example A 
______________________________________                                    
Post-emergence test                                                       
______________________________________                                    
Solvent:    5 parts by weight of acetone                                  
Emulsifier: 1 part by weight of alkylaryl polyglycol                      
            ether                                                         
______________________________________
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
Test plants which have a height of 5-15 cm are sprayed with the preparation of the active compound in such a way as to apply the particular amounts of active compound desired per unit area. The concentration of the spray liquor is so chosen that the particular amounts of active compound desired are applied in 1000 l of water/ha. After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control. The figures denote: ##EQU1##
In this test, a clearly superior activity compared with the prior art is shown, for example, by the compounds of Preparation Examples 1 and 2.
Example B 
______________________________________                                    
Pre-emergence test                                                        
______________________________________                                    
Solvent:    5 parts by weight of acetone                                  
Emulsifier: 1 part by weight of alkylaryl polyglycol                      
            ether                                                         
______________________________________
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
Seeds of the test plants are sown in normal soil and, after 24 hours, watered with the preparation of the active compound. It is expedient to keep constant the amount of water per unit area. The concentration of the active compound in the preparation is of no importance, only the amount of active compound applied per unit area being decisive. After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control. The figures denote: ##EQU2##
In this test, a powerful action against weeds combined with good tolerance by crop plants such as, for example, barley, is shown, for example, by the compound of Preparation Example 2.
USE EXAMPLES
In the second Use Examples, the following compound (C) is used as comparison substance: ##STR680##
2-(2-chloro-phenylsulphonylaminocarbonyl)-4,5-dimethyl-2,4-dihydro-3H-1,2,4-triazol-3-one (disclosed in EP-A 341,489).
Example C 
______________________________________                                    
Post-emergence test                                                       
______________________________________                                    
Solvent:    5 parts by weight of acetone                                  
Emulsifier: 1 part by weight of alkylaryl polyglycol                      
            ether                                                         
______________________________________
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
Test plants which have a height of 5-15 cm are sprayed with the preparation of the active compound in such a way as to apply the particular amounts of active compound desired per unit area. The concentration of the spray liquor is so chosen that the particular amounts of active compound desired are applied in 1,000 l of water/ha. After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control. The figures denote: ##EQU3##
In this test, a considerably more powerful action against weeds than the known compound (C) is shown, for example, by the compounds of Preparation Examples 1, 2, 3, 53, 54, 55, 56, 57, 58, 64, 65 and 67, while having, in some cases, good crop plant compatibility.
Example D 
______________________________________                                    
Pre-emergence test                                                        
______________________________________                                    
Solvent:    5 parts by weight of acetone                                  
Emulsifier: 1 part by weight of alkylaryl polyglycol                      
            ether                                                         
______________________________________
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
Seeds of the test plants are sown in normal soil and, after 24 hours, watered with the preparation of the active compound. It is expedient to keep constant the amount of water per unit area. The concentration of the active compound in the preparation is of no importance, only the amount of active compound applied per unit area being decisive. After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control. The figures denote: ##EQU4##
In this test, a considerably more powerful action against weeds than the known compound (C) is shown, for example, by the compounds of Preparation Examples 2, 54 and 69, while having, in some cases, good crop plant compatibility.
It will be understood that the specification and examples are illustrative but not limitative of the present invention and that other embodiments within the spirit and scope of the invention will suggest themselves to those skilled in the art.

Claims (5)

What is claimed is:
1. A triazolinone of the formula ##STR681## in which R2 represents amino, or represents C1 -C6 -alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, C1 -C4 -alkoxy, C1 -C4 -alkylcarbonyl or C1 -C4 -alkoxycarbonyl, or represents C3 -C6 -alkenyl or C3 -C6 -alkinyl, each of which is optionally substituted by fluorine, chlorine and/or bromine, or represents C3 -C6 -cycloalkyl which is optionally substituted by fluorine, chlorine, bromine and/or C1 -C4 -alkyl, or C1 -C7 cycloalkyl-C1 -C6 -alkyl or represents phenyl-C1 -C3 - alkyl
which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C1 -C4 -alkyl, trifluoromethyl, C1 -C4 -alkoxy and/or C1 -C4 -alkoxy-carbonyl, or represents phenyl which is substituted by fluorine, chlorine, bromine, cyano, nitro, C1 -C4 -alkyl, trifluoromethyl, C1 -C4 -alkoxy, fluorine- and/or chlorine-substituted C1 -C3 -alkoxy, C1 -C4 -alkylthio, fluorine- and/or chlorine-substituted C1 -C3 -alkylthio, C1 -C4 -alkylsulphinyl, C1 -C4 -alkylsulphonyl and/or C1 -C4 -alkoxy-carbonyl, or represents C1 -C4 -alkylamino which is optionally substituted by fluorine, cyano, C1 -C4 -alkoxy or C1 -C4 -alkoxy-carbonyl, or represents C3 -C6 -cycloalkylamino or di-(C1 -C4 -alkyl) -amino, and
R3 represents C1 -C6 -alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, C3 -C6 -cycloalkyl, C1 -C4 -alkoxy or C1 -C4 -alkoxycarbonyl, or represents C3 -C6 -alkenyl or C3 -C6 -alkinyl, each of which is optionally substituted by fluorine, chlorine and/or bromine, or represents C3 -C6 -cycloalkyl which is optionally substituted by fluorine, chlorine, bromine and/or C1 -C4 -alkyl, or represents cyclohexenyl, or represents phenyl-C1 -C3 -alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C1 -C4 -alkyl, trifluoromethyl, C1 -C4 -alkoxy and/or C1 -C4 -alkoxy-carbonyl, or represents phenyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C1 -C4 -alkyl, trifluoromethyl, C1 -C4 -alkoxy, fluorine- and/or chlorine-substituted C1 -C3 -alkoxy, C1 -C4 -alkylthio, fluorine- and/or chlorine-substituted C1 -C3 -alkylthio, C1 -C4 -alkyl-sulphinyl, C1 -C4 -alkylsulphonyl and/or C1 -C4 -alkoxy-carbonyl, provided that when R2 is methyl, R3 cannot be methyl.
2. A triazolinone according to claim 1, wherein
R2 represents C1 -C3 alkyl, C2 -C3 alkenyl or C3 -C6 -cycloalkyl and
R3 represents C1 -C6 alkyl, C2 -C6 alkenyl or C2 -C6 alkynyl.
3. A triazolinone according to claim 1, wherein
R2 represents methyl or cyclopropyl and
R3 represents methyl, ethyl, n-propyl, i-propyl, n-butyl or allyl.
4. A triazolinone according to claim 1, wherein
R2 represents ethyl or allyl and
R3 represents methyl, ethyl, n-propyl, i-propyl, n-butyl and allyl.
5. A triazolinone according to claim 1, wherein ##STR682##
US08/269,875 1988-05-09 1994-06-30 Substituted 5-alkoxy-1,2,4-triazol-3-(thi)ones Expired - Lifetime US5541337A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US08/269,875 US5541337A (en) 1989-04-13 1994-06-30 Substituted 5-alkoxy-1,2,4-triazol-3-(thi)ones
US08/637,995 US5652372A (en) 1988-05-09 1996-04-25 Substituted 5-alkoxy-1,2,4-triazol-3-(THI) ones

Applications Claiming Priority (14)

Application Number Priority Date Filing Date Title
US33777589A 1989-04-13 1989-04-13
US07/556,052 US5057144A (en) 1988-05-09 1990-07-20 Sulphonylaminocarbonyltriazolinones
DE4030063A DE4030063A1 (en) 1990-09-22 1990-09-22 SUBSTITUTED 5-ALKOXY-1,2,4, -TRIAZOL-3- (THI) ONE
DE4030063.3 1990-09-22
DE4110795.0 1991-04-04
DE4110795A DE4110795A1 (en) 1991-04-04 1991-04-04 SULFONYLAMINOCARBONYLTRIAZOLINONE WITH OXYGEN SUBSTITUTES
US07/692,439 US5094683A (en) 1988-05-09 1991-04-29 Sulphonylaminocarbonyltriazolinones
US75778591A 1991-11-11 1991-11-11
US07/816,365 US5241074A (en) 1988-05-09 1991-12-30 Sulphonylaminocarbonyltriazolinones
US85702592A 1992-03-24 1992-03-24
US07/976,185 US5356865A (en) 1990-09-22 1992-11-06 Substituted 5-alkoxy-1,2,4-triazol-3-(thi)ones
US08/031,426 US5405970A (en) 1988-05-09 1993-03-15 Sulphonylaminocarbonyltriazolinones
US4802693A 1993-04-15 1993-04-15
US08/269,875 US5541337A (en) 1989-04-13 1994-06-30 Substituted 5-alkoxy-1,2,4-triazol-3-(thi)ones

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US08/031,426 Continuation-In-Part US5405970A (en) 1988-05-09 1993-03-15 Sulphonylaminocarbonyltriazolinones
US4802693A Continuation-In-Part 1988-05-09 1993-04-15

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US6162762A (en) * 1998-01-12 2000-12-19 Novartis Crop Protection, Inc. Herbicidal composition
US6200931B1 (en) 1996-08-16 2001-03-13 Bayer Aktiengesellschaft 5,6-dihydro-(1,4,2)-Dioxazin-substituted (hetero) aryl-(oxy-, imino-, alkyl-)-sulphonylamino(thio)carbonyl-heterocyclyl derivatives, their preparation and their use as herbicides
US6297192B1 (en) 1998-01-24 2001-10-02 Bayer Aktiengesellschaft Selective herbicides based on N-aryl-triazoline(thi)ons and N-arlysulfonylamino(thio)carbonyl-triazoline(thi)ons
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US6403535B1 (en) 1998-09-24 2002-06-11 Bayer Aktiengesellschaft Substituted thiazol(in) ylideneamino sulfonylamino (thio)carbonyl-triazolinones
US6821926B1 (en) 1999-11-19 2004-11-23 Bayer Aktiengesellschaft Carbamoyl triazolinone based herbicide
US20050014809A1 (en) * 2001-11-02 2005-01-20 Ernst-Rudolf Gesing Substituted thien-3-yl-sulphonylamino(thio)carbonyl-triazolin(thi)ones
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